NPASS Compound

Structure

NPC474564 OpenBabel07101719162D 78 86 0 0 1 0 0 0 0 0999 V2000 -17.1214 2.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8486 -0.9885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9850 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6971 -0.9885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6149 -1.6499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5682 -0.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4021 -1.8916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5607 2.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1289 3.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.4093 2.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -19.6896 0.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4243 -5.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5682 -5.4368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2804 -5.4368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5682 -4.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2804 -4.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4243 -2.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5682 -2.4713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7121 1.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2804 0.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4243 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8561 1.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5212 -0.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9401 0.3055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4243 1.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8486 1.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4168 1.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6971 1.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7121 -0.9885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -17.1214 1.9770 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8486 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.1289 0.4943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.6971 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6747 -1.9554 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4243 -3.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5682 1.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2804 1.4828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7046 1.4828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2729 1.9770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.5532 1.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7121 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8561 -1.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7121 -2.9655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9925 1.4828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4168 0.4943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.8411 1.4828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -17.9775 1.4828 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -17.1214 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7046 0.4943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.1289 1.4828 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.5532 0.4943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -17.9775 0.4943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -16.2654 0.4943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5682 0.4943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9401 -1.2940 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8561 0.4943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4692 -2.9223 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7121 -3.9540 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -18.8336 1.9770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -17.1214 -0.9885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7346 -2.2609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8561 1.4828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4021 0.9030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5607 1.9770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2729 2.9655 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.4093 1.9770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -18.8336 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9925 0.4943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2729 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8411 0.4943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -16.2654 1.4828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1364 1.9770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8561 -2.4713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5607 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9850 1.9770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.4093 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7 55 1 0 0 0 0 8 66 1 0 0 0 0 9 67 1 0 0 0 0 10 68 1 0 0 0 0 11 69 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 35 2 0 0 0 0 16 35 1 0 0 0 0 17 18 2 0 0 0 0 17 35 1 0 0 0 0 18 43 1 0 0 0 0 19 22 1 0 0 0 0 19 36 2 0 0 0 0 20 21 1 0 0 0 0 20 37 1 0 0 0 0 21 54 1 0 0 0 0 22 57 1 0 0 0 0 23 24 1 0 0 0 0 23 56 1 0 0 0 0 24 58 1 0 0 0 0 25 36 1 0 0 0 0 25 37 1 0 0 0 0 26 38 1 0 0 0 0 26 44 1 0 0 0 0 27 39 1 0 0 0 0 27 45 1 0 0 0 0 28 40 1 0 0 0 0 28 46 1 0 0 0 0 29 41 1 0 0 0 0 29 42 1 0 0 0 0 30 1 1 1 0 0 0 30 47 1 0 0 0 0 30 73 1 0 0 0 0 31 2 1 6 0 0 0 31 49 1 0 0 0 0 31 70 1 0 0 0 0 32 3 1 6 0 0 0 32 50 1 0 0 0 0 32 71 1 0 0 0 0 33 4 1 6 0 0 0 33 51 1 0 0 0 0 33 72 1 0 0 0 0 34 5 1 6 0 0 0 34 56 1 0 0 0 0 34 59 1 0 0 0 0 36 54 1 0 0 0 0 37 74 1 6 0 0 0 38 49 1 0 0 0 0 38 66 1 1 0 0 0 39 50 1 0 0 0 0 39 67 1 1 0 0 0 40 51 1 0 0 0 0 40 68 1 6 0 0 0 41 54 1 6 0 0 0 41 57 1 0 0 0 0 42 55 1 6 0 0 0 42 75 1 0 0 0 0 43 60 2 0 0 0 0 43 75 1 0 0 0 0 44 70 1 0 0 0 0 44 74 1 6 0 0 0 45 71 1 0 0 0 0 45 76 1 6 0 0 0 46 72 1 0 0 0 0 46 77 1 6 0 0 0 47 52 1 0 0 0 0 47 61 1 1 0 0 0 48 52 1 0 0 0 0 48 53 1 0 0 0 0 48 62 1 6 0 0 0 49 76 1 1 0 0 0 50 77 1 1 0 0 0 51 78 1 1 0 0 0 52 69 1 1 0 0 0 53 73 1 0 0 0 0 53 78 1 1 0 0 0 54 6 1 6 0 0 0 55 56 1 1 0 0 0 56 63 1 1 0 0 0 57 58 1 1 0 0 0 57 64 1 0 0 0 0 58 55 1 6 0 0 0 58 65 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1104.59
Volume:	1094.701
LogP:	3.891
LogD:	3.03
LogS:	-4.603
# Rotatable Bonds:	17
TPSA:	258.44
# H-Bond Aceptor:	20
# H-Bond Donor:	6
# Rings:	9
# Heavy Atoms:	20

MedChem Properties

QED Drug-Likeness Score:	0.078
Synthetic Accessibility Score:	6.967
Fsp3:	0.81
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.628
MDCK Permeability:	0.00013686231977771968
Pgp-inhibitor:	0.021
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	74.10475158691406%
Volume Distribution (VD):	0.201
Pgp-substrate:	9.101153373718262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.458
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.55
CYP3A4-substrate:	0.917

ADMET: Excretion

Clearance (CL):	1.256
Half-life (T1/2):	0.234

ADMET: Toxicity

hERG Blockers:	0.899
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.431
AMES Toxicity:	0.662
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.933
Carcinogencity:	0.078
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.827

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC474564

Natural Product ID:	NPC474564
*Common Name:**	[(3S,8S,9R,10R,12R,13R,14R,17R)-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5S,6R)-3,5-Dihydroxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-4-Methoxy-6-Methyloxan-2-Yl]Oxy-8,14,17-Trihydroxy-17-[(1S)-1-Hydroxyethyl]-10,13-Dimethyl-1,2,3,4,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-12-Yl] (E)-3-Phenylprop-2-Enoate
IUPAC Name:	[(3S,8S,9R,10R,12R,13R,14R,17R)-3-[(2R,4S,5R,6R)-5-[(2S,4S,5R,6R)-5-[(2S,4R,5R,6R)-5-[(2S,3R,4S,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-8,14,17-trihydroxy-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl] (E)-3-phenylprop-2-enoate
Synonyms:
Standard InCHIKey:	IIOPSEVNHNVNNB-RJTZQLKUSA-N
Standard InCHI:	InChI=1S/C58H88O20/c1-30-47(61)52(69-11)48(62)53(73-30)78-51-33(4)72-46(28-40(51)68-10)77-50-32(3)71-45(27-39(50)67-9)76-49-31(2)70-44(26-38(49)66-8)74-37-20-21-54(6)36(25-37)19-22-57(64)41(54)29-42(75-43(60)18-17-35-15-13-12-14-16-35)55(7)56(63,34(5)59)23-24-58(55,57)65/h12-19,30-34,37-42,44-53,59,61-65H,20-29H2,1-11H3/b18-17+/t30-,31-,32-,33-,34+,37+,38+,39+,40-,41-,42-,44+,45+,46+,47+,48-,49-,50-,51-,52+,53+,54+,55-,56+,57+,58-/m1/s1
SMILES:	CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C(=CC[C@@]4([C@@H]3C[C@@H](OC(=O)/C=C/c3ccccc3)[C@]3([C@]4(O)CC[C@]3(O)[C@@H](O)C)C)O)C2)C)O[C@@H]([C@H]1O[C@H]1C[C@H](OC)[C@@H]([C@H](O1)C)O[C@H]1C[C@@H](OC)[C@@H]([C@H](O1)C)O[C@@H]1O[C@H](C)[C@@H]([C@@H]([C@H]1O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473367
PubChem CID:	44575231
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32487	leptadenia pyrotechnica	Species	Apocynaceae	Eukaryota	whole plant	Dogon region, Mali	2002-Apr	PMID[16643040]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	460.0	nM	PMID[548590]
NPT1182	Cell Line	J774.A1	Mus musculus	IC50	=	2110.0	nM	PMID[548590]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC474564 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	345
0.1-0.2	1253
0.2-0.3	2923
0.3-0.4	6120
0.4-0.5	12651
0.5-0.6	13157
0.6-0.7	4673
0.7-0.8	1448
0.8-0.85	74
0.85-0.9	19
0.9-0.95	23
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC475447
0.9929	High Similarity	NPC475218
0.9929	High Similarity	NPC476092
0.9929	High Similarity	NPC70236
0.9267	High Similarity	NPC165234
0.9267	High Similarity	NPC475536
0.9205	High Similarity	NPC475464
0.9205	High Similarity	NPC475437
0.9205	High Similarity	NPC473641
0.9205	High Similarity	NPC473797
0.9205	High Similarity	NPC475300
0.9205	High Similarity	NPC475505
0.9085	High Similarity	NPC473468
0.9085	High Similarity	NPC473557
0.9085	High Similarity	NPC475567
0.9026	High Similarity	NPC475531
0.9026	High Similarity	NPC475175
0.9026	High Similarity	NPC475198
0.894	High Similarity	NPC476784
0.8889	High Similarity	NPC475513
0.8889	High Similarity	NPC473755
0.8671	High Similarity	NPC477488
0.8667	High Similarity	NPC478123
0.8639	High Similarity	NPC111466
0.8581	High Similarity	NPC264270
0.8581	High Similarity	NPC40085
0.8528	High Similarity	NPC475613
0.8514	High Similarity	NPC471139
0.8481	Intermediate Similarity	NPC477491
0.8471	Intermediate Similarity	NPC269668
0.8429	Intermediate Similarity	NPC476971
0.8429	Intermediate Similarity	NPC476972
0.8421	Intermediate Similarity	NPC62792
0.8421	Intermediate Similarity	NPC298072
0.8387	Intermediate Similarity	NPC477472
0.8387	Intermediate Similarity	NPC477470
0.8387	Intermediate Similarity	NPC477474
0.8369	Intermediate Similarity	NPC230331
0.8357	Intermediate Similarity	NPC475933
0.8357	Intermediate Similarity	NPC470158
0.8357	Intermediate Similarity	NPC476970
0.8333	Intermediate Similarity	NPC319404
0.8333	Intermediate Similarity	NPC477467
0.8312	Intermediate Similarity	NPC69425
0.8301	Intermediate Similarity	NPC329657
0.828	Intermediate Similarity	NPC477623
0.8264	Intermediate Similarity	NPC476976
0.8258	Intermediate Similarity	NPC471176
0.8239	Intermediate Similarity	NPC478125
0.8235	Intermediate Similarity	NPC476173
0.8194	Intermediate Similarity	NPC476977
0.8188	Intermediate Similarity	NPC325078
0.8176	Intermediate Similarity	NPC478124
0.8156	Intermediate Similarity	NPC471758
0.8153	Intermediate Similarity	NPC318447
0.8153	Intermediate Similarity	NPC322048
0.8143	Intermediate Similarity	NPC473871
0.8143	Intermediate Similarity	NPC473870
0.8141	Intermediate Similarity	NPC469398
0.8117	Intermediate Similarity	NPC475417
0.8117	Intermediate Similarity	NPC475561
0.8112	Intermediate Similarity	NPC58061
0.8099	Intermediate Similarity	NPC473111
0.8099	Intermediate Similarity	NPC473110
0.8099	Intermediate Similarity	NPC45821
0.8089	Intermediate Similarity	NPC323001
0.8089	Intermediate Similarity	NPC326235
0.8085	Intermediate Similarity	NPC470815
0.8079	Intermediate Similarity	NPC284957
0.8077	Intermediate Similarity	NPC77310
0.8077	Intermediate Similarity	NPC471135
0.8077	Intermediate Similarity	NPC472658
0.8077	Intermediate Similarity	NPC472657
0.8071	Intermediate Similarity	NPC70973
0.8071	Intermediate Similarity	NPC473889
0.8056	Intermediate Similarity	NPC93632
0.805	Intermediate Similarity	NPC323356
0.805	Intermediate Similarity	NPC471138
0.805	Intermediate Similarity	NPC326328
0.805	Intermediate Similarity	NPC309991
0.8028	Intermediate Similarity	NPC145287
0.8028	Intermediate Similarity	NPC473083
0.8028	Intermediate Similarity	NPC114927
0.8028	Intermediate Similarity	NPC284022
0.8026	Intermediate Similarity	NPC204644
0.8025	Intermediate Similarity	NPC34066
0.8025	Intermediate Similarity	NPC469422
0.8025	Intermediate Similarity	NPC469456
0.8014	Intermediate Similarity	NPC12016
0.8	Intermediate Similarity	NPC469448
0.8	Intermediate Similarity	NPC311175
0.8	Intermediate Similarity	NPC37641
0.7988	Intermediate Similarity	NPC477473
0.7988	Intermediate Similarity	NPC477466
0.7988	Intermediate Similarity	NPC477471
0.7988	Intermediate Similarity	NPC477469
0.7975	Intermediate Similarity	NPC475548
0.7975	Intermediate Similarity	NPC290683
0.7975	Intermediate Similarity	NPC475638
0.7958	Intermediate Similarity	NPC472373
0.7949	Intermediate Similarity	NPC469415
0.7939	Intermediate Similarity	NPC286809
0.7927	Intermediate Similarity	NPC102465
0.7917	Intermediate Similarity	NPC267733
0.7917	Intermediate Similarity	NPC276047
0.7914	Intermediate Similarity	NPC135369
0.7901	Intermediate Similarity	NPC150893
0.7901	Intermediate Similarity	NPC329960
0.7901	Intermediate Similarity	NPC295408
0.7887	Intermediate Similarity	NPC179261
0.7885	Intermediate Similarity	NPC222102
0.7885	Intermediate Similarity	NPC303429
0.7881	Intermediate Similarity	NPC473440
0.7877	Intermediate Similarity	NPC475138
0.7875	Intermediate Similarity	NPC469399
0.7872	Intermediate Similarity	NPC300827
0.7872	Intermediate Similarity	NPC473439
0.7872	Intermediate Similarity	NPC117445
0.7872	Intermediate Similarity	NPC308262
0.7872	Intermediate Similarity	NPC208193
0.7871	Intermediate Similarity	NPC320734
0.7862	Intermediate Similarity	NPC175333
0.7857	Intermediate Similarity	NPC471104
0.7857	Intermediate Similarity	NPC29704
0.7857	Intermediate Similarity	NPC158663
0.7857	Intermediate Similarity	NPC171525
0.7857	Intermediate Similarity	NPC469349
0.7857	Intermediate Similarity	NPC70403
0.7857	Intermediate Similarity	NPC470159
0.7857	Intermediate Similarity	NPC472568
0.7857	Intermediate Similarity	NPC96903
0.7857	Intermediate Similarity	NPC472575
0.7857	Intermediate Similarity	NPC200471
0.7857	Intermediate Similarity	NPC177940
0.7857	Intermediate Similarity	NPC472572
0.7857	Intermediate Similarity	NPC96447
0.7857	Intermediate Similarity	NPC470157
0.7857	Intermediate Similarity	NPC470814
0.7857	Intermediate Similarity	NPC174982
0.7857	Intermediate Similarity	NPC472571
0.7857	Intermediate Similarity	NPC184817
0.7857	Intermediate Similarity	NPC473088
0.7857	Intermediate Similarity	NPC476973
0.7847	Intermediate Similarity	NPC473082
0.7834	Intermediate Similarity	NPC96308
0.7829	Intermediate Similarity	NPC97947
0.7829	Intermediate Similarity	NPC118080
0.7829	Intermediate Similarity	NPC41481
0.7829	Intermediate Similarity	NPC291599
0.7829	Intermediate Similarity	NPC27377
0.7829	Intermediate Similarity	NPC87448
0.7829	Intermediate Similarity	NPC472576
0.7829	Intermediate Similarity	NPC16912
0.7821	Intermediate Similarity	NPC92293
0.7821	Intermediate Similarity	NPC301556
0.7821	Intermediate Similarity	NPC270590
0.7821	Intermediate Similarity	NPC471101
0.7821	Intermediate Similarity	NPC266265
0.7817	Intermediate Similarity	NPC473749
0.7817	Intermediate Similarity	NPC475328
0.7808	Intermediate Similarity	NPC471024
0.7806	Intermediate Similarity	NPC478263
0.7806	Intermediate Similarity	NPC473602
0.7806	Intermediate Similarity	NPC312393
0.7806	Intermediate Similarity	NPC474935
0.7801	Intermediate Similarity	NPC474423
0.7801	Intermediate Similarity	NPC193893
0.7801	Intermediate Similarity	NPC74259
0.7801	Intermediate Similarity	NPC264336
0.7799	Intermediate Similarity	NPC5115
0.7793	Intermediate Similarity	NPC204214
0.7793	Intermediate Similarity	NPC231888
0.7793	Intermediate Similarity	NPC35338
0.7793	Intermediate Similarity	NPC63404
0.7793	Intermediate Similarity	NPC198918
0.7793	Intermediate Similarity	NPC290276
0.7793	Intermediate Similarity	NPC92283
0.7793	Intermediate Similarity	NPC10883
0.7793	Intermediate Similarity	NPC124878
0.7793	Intermediate Similarity	NPC10121
0.7792	Intermediate Similarity	NPC70716
0.7792	Intermediate Similarity	NPC125106
0.7792	Intermediate Similarity	NPC57628
0.7792	Intermediate Similarity	NPC241951
0.7792	Intermediate Similarity	NPC476974
0.7792	Intermediate Similarity	NPC95810
0.7792	Intermediate Similarity	NPC475759
0.7792	Intermediate Similarity	NPC25768
0.7792	Intermediate Similarity	NPC472573
0.7792	Intermediate Similarity	NPC472570
0.7792	Intermediate Similarity	NPC95265
0.7792	Intermediate Similarity	NPC475122
0.7792	Intermediate Similarity	NPC11685
0.7792	Intermediate Similarity	NPC472569
0.7792	Intermediate Similarity	NPC470152
0.7792	Intermediate Similarity	NPC188865
0.7792	Intermediate Similarity	NPC163719
0.7786	Intermediate Similarity	NPC473566
0.7786	Intermediate Similarity	NPC475358
0.7786	Intermediate Similarity	NPC473860

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC474564 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	791
0.2-0.3	1988
0.3-0.4	3462
0.4-0.5	1928
0.5-0.6	597
0.6-0.7	93
0.7-0.8	18
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.773	Intermediate Similarity	NPD8378	Approved
0.773	Intermediate Similarity	NPD8033	Approved
0.773	Intermediate Similarity	NPD8296	Approved
0.773	Intermediate Similarity	NPD8380	Approved
0.773	Intermediate Similarity	NPD8379	Approved
0.773	Intermediate Similarity	NPD8335	Approved
0.766	Intermediate Similarity	NPD8294	Approved
0.766	Intermediate Similarity	NPD8377	Approved
0.7619	Intermediate Similarity	NPD7799	Discontinued
0.7606	Intermediate Similarity	NPD7503	Approved
0.7589	Intermediate Similarity	NPD7516	Approved
0.7518	Intermediate Similarity	NPD7327	Approved
0.7518	Intermediate Similarity	NPD7328	Approved
0.7368	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7236	Approved
0.7197	Intermediate Similarity	NPD7266	Discontinued
0.7178	Intermediate Similarity	NPD7239	Suspended
0.7172	Intermediate Similarity	NPD7741	Discontinued
0.7032	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5126	Approved
0.6959	Remote Similarity	NPD5125	Phase 3
0.6949	Remote Similarity	NPD8368	Discontinued
0.6933	Remote Similarity	NPD7507	Approved
0.6927	Remote Similarity	NPD8407	Phase 2
0.6914	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7319	Approved
0.6889	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8133	Approved
0.6854	Remote Similarity	NPD7685	Pre-registration
0.6821	Remote Similarity	NPD8127	Discontinued
0.6818	Remote Similarity	NPD7228	Approved
0.6784	Remote Similarity	NPD7058	Phase 2
0.6784	Remote Similarity	NPD7057	Phase 3
0.6765	Remote Similarity	NPD8455	Phase 2
0.676	Remote Similarity	NPD7240	Approved
0.6759	Remote Similarity	NPD7094	Approved
0.6759	Remote Similarity	NPD6858	Approved
0.669	Remote Similarity	NPD6685	Approved
0.6685	Remote Similarity	NPD8360	Approved
0.6685	Remote Similarity	NPD8435	Approved
0.6685	Remote Similarity	NPD8312	Approved
0.6685	Remote Similarity	NPD8313	Approved
0.6685	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6646	Remote Similarity	NPD7961	Discontinued
0.6646	Remote Similarity	NPD8166	Discontinued
0.6624	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4198	Discontinued
0.6613	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6674	Discontinued
0.6581	Remote Similarity	NPD3094	Phase 2
0.6579	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD8434	Phase 2
0.6556	Remote Similarity	NPD8517	Approved
0.6556	Remote Similarity	NPD8516	Approved
0.6556	Remote Similarity	NPD8515	Approved
0.6545	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7736	Approved
0.6512	Remote Similarity	NPD37	Approved
0.65	Remote Similarity	NPD4140	Approved
0.6497	Remote Similarity	NPD5736	Approved
0.6494	Remote Similarity	NPD4965	Approved
0.6494	Remote Similarity	NPD4967	Phase 2
0.6494	Remote Similarity	NPD4966	Approved
0.6491	Remote Similarity	NPD7028	Phase 2
0.6488	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5765	Approved
0.6463	Remote Similarity	NPD6912	Phase 3
0.6447	Remote Similarity	NPD8513	Phase 3
0.6443	Remote Similarity	NPD7497	Discontinued
0.6441	Remote Similarity	NPD7199	Phase 2
0.642	Remote Similarity	NPD6234	Discontinued
0.6414	Remote Similarity	NPD6686	Approved
0.641	Remote Similarity	NPD8320	Phase 1
0.641	Remote Similarity	NPD8319	Approved
0.6398	Remote Similarity	NPD8150	Discontinued
0.6387	Remote Similarity	NPD8485	Approved
0.638	Remote Similarity	NPD7097	Phase 1
0.6374	Remote Similarity	NPD1653	Approved
0.6364	Remote Similarity	NPD8328	Phase 3
0.6364	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD5735	Approved
0.6354	Remote Similarity	NPD7699	Phase 2
0.6354	Remote Similarity	NPD7700	Phase 2
0.6353	Remote Similarity	NPD6273	Approved
0.6347	Remote Similarity	NPD7625	Phase 1
0.6345	Remote Similarity	NPD6412	Phase 2
0.6335	Remote Similarity	NPD6663	Approved
0.6323	Remote Similarity	NPD3092	Approved
0.631	Remote Similarity	NPD6190	Approved
0.6284	Remote Similarity	NPD7074	Phase 3
0.6278	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7458	Discontinued
0.6242	Remote Similarity	NPD969	Suspended
0.623	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD2629	Approved
0.6209	Remote Similarity	NPD7610	Discontinued
0.6198	Remote Similarity	NPD6535	Approved
0.6198	Remote Similarity	NPD6534	Approved
0.6197	Remote Similarity	NPD7638	Approved
0.6196	Remote Similarity	NPD3620	Phase 2
0.6196	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD7472	Approved
0.6194	Remote Similarity	NPD3095	Discontinued
0.6194	Remote Similarity	NPD6370	Approved
0.6193	Remote Similarity	NPD5761	Phase 2
0.6193	Remote Similarity	NPD7435	Discontinued
0.6193	Remote Similarity	NPD5760	Phase 2
0.6193	Remote Similarity	NPD7680	Approved
0.6184	Remote Similarity	NPD7115	Discovery
0.6183	Remote Similarity	NPD7808	Phase 3
0.6175	Remote Similarity	NPD3751	Discontinued
0.6169	Remote Similarity	NPD3091	Approved
0.6163	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD6010	Discontinued
0.6154	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7640	Approved
0.6154	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7639	Approved
0.6149	Remote Similarity	NPD7055	Discontinued
0.6149	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD7054	Approved
0.6141	Remote Similarity	NPD5844	Phase 1
0.6139	Remote Similarity	NPD7783	Phase 2
0.6139	Remote Similarity	NPD8293	Discontinued
0.6139	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD6647	Phase 2
0.6133	Remote Similarity	NPD8297	Approved
0.6133	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD6764	Approved
0.6129	Remote Similarity	NPD7251	Discontinued
0.6129	Remote Similarity	NPD6559	Discontinued
0.6129	Remote Similarity	NPD6765	Approved
0.6121	Remote Similarity	NPD6653	Approved
0.6121	Remote Similarity	NPD6353	Approved
0.6119	Remote Similarity	NPD8151	Discontinued
0.6115	Remote Similarity	NPD7492	Approved
0.6111	Remote Similarity	NPD7697	Approved
0.6111	Remote Similarity	NPD7696	Phase 3
0.6111	Remote Similarity	NPD7698	Approved
0.6111	Remote Similarity	NPD5344	Discontinued
0.6105	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD7874	Approved
0.6087	Remote Similarity	NPD7084	Phase 3
0.6078	Remote Similarity	NPD6009	Approved
0.6078	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD6616	Approved
0.6075	Remote Similarity	NPD6797	Phase 2
0.6071	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6005	Phase 3
0.6071	Remote Similarity	NPD6004	Phase 3
0.6071	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6002	Phase 3
0.607	Remote Similarity	NPD7701	Phase 2
0.6065	Remote Similarity	NPD6319	Approved
0.6065	Remote Similarity	NPD7009	Phase 2
0.6065	Remote Similarity	NPD6054	Approved
0.6061	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6823	Phase 2
0.6061	Remote Similarity	NPD5124	Phase 1
0.6059	Remote Similarity	NPD4628	Phase 3
0.6059	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD3787	Discontinued
0.6042	Remote Similarity	NPD6648	Approved
0.6041	Remote Similarity	NPD6778	Approved
0.6041	Remote Similarity	NPD6782	Approved
0.6041	Remote Similarity	NPD6781	Approved
0.6041	Remote Similarity	NPD6777	Approved
0.6041	Remote Similarity	NPD6780	Approved
0.6041	Remote Similarity	NPD6779	Approved
0.6041	Remote Similarity	NPD6776	Approved
0.604	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD5327	Phase 3
0.6038	Remote Similarity	NPD7078	Approved
0.6029	Remote Similarity	NPD8462	Phase 1
0.6025	Remote Similarity	NPD4624	Approved
0.6012	Remote Similarity	NPD7008	Discontinued
0.6012	Remote Similarity	NPD8450	Suspended
0.6011	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6784	Approved
0.6	Remote Similarity	NPD7871	Phase 2
0.6	Remote Similarity	NPD7870	Phase 2
0.6	Remote Similarity	NPD6785	Approved
0.5989	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD4632	Approved
0.598	Remote Similarity	NPD7801	Approved
0.5976	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.596	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD8171	Discontinued
0.5954	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD8449	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data