NPASS Compound

Structure

CID308459 OpenBabel06191716112D 77 85 0 0 1 0 0 0 0 0999 V2000 -1.6716 10.7716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3816 8.0848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0488 5.5639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6940 5.6150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4861 6.5931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3271 9.4983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9149 8.6893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8409 6.5420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6329 7.5202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1588 3.9677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2567 4.5857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 -5.4068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2567 -2.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 0.4915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9594 -1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5671 9.7771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9509 4.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5351 6.9022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3761 9.1893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3271 7.8803 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7919 6.2330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4646 3.6076 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9594 -0.4915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4156 3.2986 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -5.8983 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4054 -2.9492 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8513 0.4915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7027 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1081 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -6.8814 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4054 -3.9322 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7027 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8513 -7.3729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5540 -1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2567 -0.4915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7027 -6.8814 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4054 -0.9831 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7027 -3.9322 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7027 -0.9831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5540 -4.4237 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7027 -0.9831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8513 -1.4746 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2567 -1.4746 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4054 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7027 -5.8983 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7027 -2.9492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9831 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3761 8.1893 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9998 5.2549 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8513 -4.4237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1081 -2.9492 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7027 1.9661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6535 9.3704 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7214 2.9385 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8108 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1081 0.9831 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 -7.3729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2567 -4.4237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5540 0.4915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 -8.3559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5540 -2.4576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4054 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5540 -7.3729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 -1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 -4.4237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1081 -1.9661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2567 0.4915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 -5.4068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5540 -2.4576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5540 0.4915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8513 -1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5540 -5.4068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4054 -1.9661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 -2.4576 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 4 5 1 0 0 0 0 4 18 2 0 0 0 0 6 7 1 0 0 0 0 6 20 2 0 0 0 0 7 21 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 49 1 0 0 0 0 10 18 1 0 0 0 0 10 25 1 0 0 0 0 11 23 1 0 0 0 0 11 50 1 0 0 0 0 12 51 1 0 0 0 0 13 52 1 0 0 0 0 14 53 1 0 0 0 0 15 54 1 0 0 0 0 16 24 1 0 0 0 0 16 68 1 0 0 0 0 17 20 1 0 0 0 0 17 55 2 0 0 0 0 18 50 1 0 0 0 0 19 5 1 1 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 49 1 0 0 0 0 21 49 1 6 0 0 0 22 50 1 6 0 0 0 23 25 1 0 0 0 0 23 56 1 1 0 0 0 24 30 1 0 0 0 0 24 57 1 1 0 0 0 25 69 1 6 0 0 0 26 12 1 6 0 0 0 26 31 1 0 0 0 0 26 70 1 0 0 0 0 27 13 1 1 0 0 0 27 32 1 0 0 0 0 27 71 1 0 0 0 0 28 14 1 1 0 0 0 28 33 1 0 0 0 0 28 72 1 0 0 0 0 29 15 1 1 0 0 0 29 40 1 0 0 0 0 29 73 1 0 0 0 0 30 36 1 0 0 0 0 30 58 1 6 0 0 0 31 34 1 0 0 0 0 31 59 1 1 0 0 0 32 41 1 0 0 0 0 32 60 1 6 0 0 0 33 42 1 0 0 0 0 33 61 1 6 0 0 0 34 37 1 0 0 0 0 34 62 1 6 0 0 0 35 38 1 0 0 0 0 35 40 1 0 0 0 0 35 63 1 1 0 0 0 36 44 1 0 0 0 0 36 64 1 1 0 0 0 37 46 1 0 0 0 0 37 65 1 1 0 0 0 38 45 1 0 0 0 0 38 66 1 6 0 0 0 39 41 1 0 0 0 0 39 47 1 0 0 0 0 39 67 1 6 0 0 0 40 74 1 1 0 0 0 41 75 1 1 0 0 0 42 43 1 0 0 0 0 42 76 1 1 0 0 0 43 48 1 0 0 0 0 43 77 1 6 0 0 0 44 68 1 0 0 0 0 44 76 1 6 0 0 0 45 69 1 1 0 0 0 45 73 1 0 0 0 0 46 70 1 0 0 0 0 46 75 1 6 0 0 0 47 71 1 0 0 0 0 47 77 1 1 0 0 0 48 72 1 0 0 0 0 48 74 1 1 0 0 0 49 2 1 6 0 0 0 50 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1110.47
Volume:	1025.774
LogP:	-1.619
LogD:	-1.182
LogS:	-2.354
# Rotatable Bonds:	15
TPSA:	433.05
# H-Bond Aceptor:	27
# H-Bond Donor:	16
# Rings:	9
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	6.939
Fsp3:	0.9
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.492
MDCK Permeability:	0.00046365929301828146
Pgp-inhibitor:	0.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.8
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.316
Plasma Protein Binding (PPB):	47.478057861328125%
Volume Distribution (VD):	-0.171
Pgp-substrate:	18.49599266052246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.005
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	-0.133
Half-life (T1/2):	0.828

ADMET: Toxicity

hERG Blockers:	0.49
Human Hepatotoxicity (H-HT):	0.16
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.4
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.661

Download Data

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

Natural Product: NPC308459

Natural Product ID:	NPC308459
*Common Name:**	3Beta-[(O-Beta-D-Glucopyranosyl-(1->3)-O-Beta-D-Glucopyranosyl-(1->2)-O-[Beta-D-Xylopyranosyl-(1->3)]-O-Beta-D-Glucopyranosyl-(1->4)-Beta-D-Galactopyranosyl)Oxy]-2Alpha-Hydroxypregna-5,16-Dien-20-One
IUPAC Name:	1-[(2R,3R,8R,9S,10R,13S,14S)-3-[(2R,3R,4R,5R,6R)-5-[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
Synonyms:
Standard InCHIKey:	AZDNJBBUCLAIIW-IYCNBSOYSA-N
Standard InCHI:	InChI=1S/C50H78O27/c1-17(55)20-6-7-21-19-5-4-18-10-25(23(56)11-50(18,3)22(19)8-9-49(20,21)2)69-45-38(66)35(63)40(29(15-54)73-45)74-48-43(42(33(61)28(14-53)72-48)76-44-36(64)30(58)24(57)16-68-44)77-47-39(67)41(32(60)27(13-52)71-47)75-46-37(65)34(62)31(59)26(12-51)70-46/h4,6,19,21-48,51-54,56-67H,5,7-16H2,1-3H3/t19-,21-,22-,23+,24+,25+,26+,27+,28+,29+,30-,31+,32+,33+,34-,35+,36+,37+,38+,39+,40-,41-,42-,43+,44-,45+,46-,47-,48-,49+,50-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2CC3=CC[C@@H]4[C@@H]([C@]3(C[C@H]2O)C)CC[C@]2([C@H]4CC=C2C(=O)C)C)[C@@H]([C@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448132
PubChem CID:	11094376
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
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[11170659]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12502329]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27323	Cestrum nocturnum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
LD50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	LD50	=	192.0	ug ml-1	PMID[530491]

☑ 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 NPC308459 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	270
0.1-0.2	1678
0.2-0.3	5070
0.3-0.4	10497
0.4-0.5	11349
0.5-0.6	6897
0.6-0.7	4181
0.7-0.8	1837
0.8-0.85	480
0.85-0.9	298
0.9-0.95	138
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9554	High Similarity	NPC190939
0.9554	High Similarity	NPC197003
0.9545	High Similarity	NPC165439
0.9217	High Similarity	NPC476675
0.913	High Similarity	NPC129393
0.9115	High Similarity	NPC279638
0.8983	High Similarity	NPC473505
0.8983	High Similarity	NPC248202
0.8898	High Similarity	NPC256983
0.8889	High Similarity	NPC476672
0.886	High Similarity	NPC74727
0.885	High Similarity	NPC474265
0.885	High Similarity	NPC210420
0.8814	High Similarity	NPC15918
0.8814	High Similarity	NPC94072
0.8814	High Similarity	NPC305771
0.8814	High Similarity	NPC169816
0.8803	High Similarity	NPC476670
0.8793	High Similarity	NPC470514
0.8793	High Similarity	NPC470513
0.8783	High Similarity	NPC472718
0.8772	High Similarity	NPC260665
0.875	High Similarity	NPC246205
0.8729	High Similarity	NPC476543
0.8729	High Similarity	NPC182900
0.8729	High Similarity	NPC476544
0.8729	High Similarity	NPC476545
0.8729	High Similarity	NPC249553
0.8729	High Similarity	NPC475182
0.8718	High Similarity	NPC473401
0.8718	High Similarity	NPC477464
0.8707	High Similarity	NPC148417
0.8707	High Similarity	NPC110633
0.8707	High Similarity	NPC136768
0.8696	High Similarity	NPC57484
0.8696	High Similarity	NPC71065
0.8696	High Similarity	NPC67857
0.8696	High Similarity	NPC79643
0.8696	High Similarity	NPC76972
0.8696	High Similarity	NPC123199
0.8696	High Similarity	NPC60557
0.8696	High Similarity	NPC475160
0.8696	High Similarity	NPC261506
0.8696	High Similarity	NPC473882
0.8696	High Similarity	NPC298034
0.8696	High Similarity	NPC305981
0.8696	High Similarity	NPC293330
0.8696	High Similarity	NPC54636
0.8696	High Similarity	NPC4328
0.8696	High Similarity	NPC309907
0.8696	High Similarity	NPC474557
0.8696	High Similarity	NPC471385
0.8696	High Similarity	NPC471550
0.8696	High Similarity	NPC202828
0.8696	High Similarity	NPC224381
0.8696	High Similarity	NPC102088
0.8696	High Similarity	NPC41061
0.8696	High Similarity	NPC469782
0.8696	High Similarity	NPC204414
0.8696	High Similarity	NPC65105
0.8696	High Similarity	NPC43550
0.8696	High Similarity	NPC227551
0.8696	High Similarity	NPC476068
0.8696	High Similarity	NPC236638
0.8696	High Similarity	NPC161717
0.8696	High Similarity	NPC100639
0.8696	High Similarity	NPC475140
0.8696	High Similarity	NPC473714
0.8696	High Similarity	NPC250247
0.8696	High Similarity	NPC294453
0.8696	High Similarity	NPC70809
0.8696	High Similarity	NPC119592
0.8673	High Similarity	NPC154856
0.8673	High Similarity	NPC52241
0.8673	High Similarity	NPC475317
0.8667	High Similarity	NPC473474
0.8667	High Similarity	NPC476674
0.8644	High Similarity	NPC475187
0.8632	High Similarity	NPC36831
0.8632	High Similarity	NPC237191
0.8632	High Similarity	NPC475899
0.8621	High Similarity	NPC471384
0.8621	High Similarity	NPC161674
0.8609	High Similarity	NPC473343
0.8609	High Similarity	NPC241909
0.8609	High Similarity	NPC295823
0.8609	High Similarity	NPC114304
0.8609	High Similarity	NPC62696
0.8609	High Similarity	NPC163183
0.8609	High Similarity	NPC46665
0.8609	High Similarity	NPC258885
0.8609	High Similarity	NPC133818
0.8609	High Similarity	NPC174720
0.8609	High Similarity	NPC323341
0.8609	High Similarity	NPC134835
0.8609	High Similarity	NPC293038
0.8609	High Similarity	NPC192600
0.8609	High Similarity	NPC251263
0.8609	High Similarity	NPC114287
0.8609	High Similarity	NPC151543
0.8609	High Similarity	NPC150400
0.8609	High Similarity	NPC155410
0.8609	High Similarity	NPC124296
0.8609	High Similarity	NPC475287
0.8609	High Similarity	NPC166422
0.8609	High Similarity	NPC219180
0.8609	High Similarity	NPC251309
0.8609	High Similarity	NPC473826
0.8609	High Similarity	NPC96641
0.8609	High Similarity	NPC73318
0.8609	High Similarity	NPC309714
0.8609	High Similarity	NPC475467
0.8596	High Similarity	NPC263827
0.8596	High Similarity	NPC285410
0.8596	High Similarity	NPC250481
0.8595	High Similarity	NPC476673
0.8584	High Similarity	NPC302057
0.8583	High Similarity	NPC160084
0.8583	High Similarity	NPC476542
0.8571	High Similarity	NPC293031
0.8571	High Similarity	NPC275225
0.8571	High Similarity	NPC68767
0.8571	High Similarity	NPC477463
0.8571	High Similarity	NPC51099
0.8559	High Similarity	NPC161738
0.8559	High Similarity	NPC471577
0.8547	High Similarity	NPC68175
0.8547	High Similarity	NPC470876
0.8547	High Similarity	NPC123522
0.8547	High Similarity	NPC286457
0.8547	High Similarity	NPC220160
0.8547	High Similarity	NPC33012
0.8547	High Similarity	NPC477252
0.8547	High Similarity	NPC85154
0.8547	High Similarity	NPC309223
0.8547	High Similarity	NPC191827
0.8547	High Similarity	NPC471580
0.8547	High Similarity	NPC475209
0.8547	High Similarity	NPC104137
0.8547	High Similarity	NPC309433
0.8547	High Similarity	NPC475514
0.8547	High Similarity	NPC69811
0.8547	High Similarity	NPC185466
0.8547	High Similarity	NPC473452
0.8547	High Similarity	NPC102505
0.8547	High Similarity	NPC8524
0.8525	High Similarity	NPC470516
0.8522	High Similarity	NPC207845
0.8522	High Similarity	NPC101744
0.8522	High Similarity	NPC473373
0.8522	High Similarity	NPC475504
0.8522	High Similarity	NPC233003
0.8522	High Similarity	NPC471383
0.8522	High Similarity	NPC32361
0.8522	High Similarity	NPC210569
0.8522	High Similarity	NPC292677
0.8522	High Similarity	NPC109079
0.8522	High Similarity	NPC10320
0.8522	High Similarity	NPC79718
0.8522	High Similarity	NPC469946
0.8522	High Similarity	NPC139044
0.8522	High Similarity	NPC139894
0.8522	High Similarity	NPC244431
0.8522	High Similarity	NPC102439
0.8522	High Similarity	NPC31896
0.8522	High Similarity	NPC471967
0.8522	High Similarity	NPC104400
0.8522	High Similarity	NPC473383
0.8522	High Similarity	NPC104071
0.8522	High Similarity	NPC257468
0.8522	High Similarity	NPC324875
0.8522	High Similarity	NPC276093
0.8522	High Similarity	NPC475516
0.8522	High Similarity	NPC472719
0.8522	High Similarity	NPC263359
0.8522	High Similarity	NPC477253
0.8522	High Similarity	NPC130427
0.8512	High Similarity	NPC30188
0.8512	High Similarity	NPC177820
0.85	High Similarity	NPC475431
0.85	High Similarity	NPC156789
0.8496	Intermediate Similarity	NPC295389
0.8487	Intermediate Similarity	NPC142151
0.8487	Intermediate Similarity	NPC267694
0.8487	Intermediate Similarity	NPC268184
0.8487	Intermediate Similarity	NPC153673
0.8487	Intermediate Similarity	NPC144644
0.8487	Intermediate Similarity	NPC37860
0.8487	Intermediate Similarity	NPC110385
0.848	Intermediate Similarity	NPC102015
0.8475	Intermediate Similarity	NPC86020
0.8475	Intermediate Similarity	NPC475632
0.8462	Intermediate Similarity	NPC160415
0.8462	Intermediate Similarity	NPC288205
0.8462	Intermediate Similarity	NPC75287
0.8462	Intermediate Similarity	NPC51465
0.8462	Intermediate Similarity	NPC305267
0.8462	Intermediate Similarity	NPC476992
0.8462	Intermediate Similarity	NPC58448
0.8462	Intermediate Similarity	NPC26626

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 NPC308459 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	2011
0.2-0.3	3921
0.3-0.4	1988
0.4-0.5	538
0.5-0.6	272
0.6-0.7	139
0.7-0.8	27
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8407	Intermediate Similarity	NPD6412	Phase 2
0.813	Intermediate Similarity	NPD8328	Phase 3
0.8103	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD8133	Approved
0.7863	Intermediate Similarity	NPD6686	Approved
0.7742	Intermediate Similarity	NPD8377	Approved
0.7742	Intermediate Similarity	NPD8294	Approved
0.768	Intermediate Similarity	NPD8296	Approved
0.768	Intermediate Similarity	NPD8380	Approved
0.768	Intermediate Similarity	NPD8335	Approved
0.768	Intermediate Similarity	NPD8033	Approved
0.768	Intermediate Similarity	NPD8379	Approved
0.768	Intermediate Similarity	NPD8378	Approved
0.7642	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6370	Approved
0.7597	Intermediate Similarity	NPD7736	Approved
0.7578	Intermediate Similarity	NPD7507	Approved
0.746	Intermediate Similarity	NPD6054	Approved
0.7458	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7319	Approved
0.7402	Intermediate Similarity	NPD7503	Approved
0.7385	Intermediate Similarity	NPD8293	Discontinued
0.7381	Intermediate Similarity	NPD7516	Approved
0.7323	Intermediate Similarity	NPD6059	Approved
0.7317	Intermediate Similarity	NPD8297	Approved
0.7317	Intermediate Similarity	NPD6882	Approved
0.7302	Intermediate Similarity	NPD7327	Approved
0.7302	Intermediate Similarity	NPD7328	Approved
0.7266	Intermediate Similarity	NPD8517	Approved
0.7266	Intermediate Similarity	NPD6015	Approved
0.7266	Intermediate Similarity	NPD8516	Approved
0.7266	Intermediate Similarity	NPD6016	Approved
0.7266	Intermediate Similarity	NPD8515	Approved
0.7231	Intermediate Similarity	NPD7492	Approved
0.7222	Intermediate Similarity	NPD6009	Approved
0.7209	Intermediate Similarity	NPD5988	Approved
0.7188	Intermediate Similarity	NPD6319	Approved
0.7176	Intermediate Similarity	NPD6616	Approved
0.7154	Intermediate Similarity	NPD6067	Discontinued
0.7132	Intermediate Similarity	NPD8513	Phase 3
0.713	Intermediate Similarity	NPD7748	Approved
0.7121	Intermediate Similarity	NPD7078	Approved
0.712	Intermediate Similarity	NPD4632	Approved
0.7097	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7902	Approved
0.7087	Intermediate Similarity	NPD7115	Discovery
0.7043	Intermediate Similarity	NPD6399	Phase 3
0.6992	Remote Similarity	NPD6899	Approved
0.6992	Remote Similarity	NPD6881	Approved
0.6967	Remote Similarity	NPD5739	Approved
0.6967	Remote Similarity	NPD6675	Approved
0.6967	Remote Similarity	NPD6402	Approved
0.6967	Remote Similarity	NPD7128	Approved
0.696	Remote Similarity	NPD6650	Approved
0.696	Remote Similarity	NPD8130	Phase 1
0.696	Remote Similarity	NPD6649	Approved
0.6957	Remote Similarity	NPD7515	Phase 2
0.6957	Remote Similarity	NPD6079	Approved
0.6937	Remote Similarity	NPD4786	Approved
0.6935	Remote Similarity	NPD6373	Approved
0.6935	Remote Similarity	NPD6372	Approved
0.6934	Remote Similarity	NPD8450	Suspended
0.693	Remote Similarity	NPD5328	Approved
0.6911	Remote Similarity	NPD5697	Approved
0.6897	Remote Similarity	NPD8171	Discontinued
0.688	Remote Similarity	NPD4634	Approved
0.688	Remote Similarity	NPD6883	Approved
0.688	Remote Similarity	NPD7290	Approved
0.688	Remote Similarity	NPD7102	Approved
0.6861	Remote Similarity	NPD8449	Approved
0.6855	Remote Similarity	NPD7320	Approved
0.6838	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7900	Approved
0.6833	Remote Similarity	NPD4696	Approved
0.6833	Remote Similarity	NPD5285	Approved
0.6833	Remote Similarity	NPD5286	Approved
0.6825	Remote Similarity	NPD6617	Approved
0.6825	Remote Similarity	NPD6869	Approved
0.6825	Remote Similarity	NPD6847	Approved
0.6815	Remote Similarity	NPD6033	Approved
0.6814	Remote Similarity	NPD3618	Phase 1
0.6807	Remote Similarity	NPD4755	Approved
0.6807	Remote Similarity	NPD6084	Phase 2
0.6807	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6012	Approved
0.68	Remote Similarity	NPD6013	Approved
0.68	Remote Similarity	NPD6014	Approved
0.68	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5701	Approved
0.6767	Remote Similarity	NPD7604	Phase 2
0.6757	Remote Similarity	NPD3667	Approved
0.6752	Remote Similarity	NPD4202	Approved
0.675	Remote Similarity	NPD7638	Approved
0.6742	Remote Similarity	NPD5983	Phase 2
0.6723	Remote Similarity	NPD5221	Approved
0.6723	Remote Similarity	NPD5222	Approved
0.6723	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5225	Approved
0.6721	Remote Similarity	NPD4633	Approved
0.6721	Remote Similarity	NPD5226	Approved
0.6721	Remote Similarity	NPD5211	Phase 2
0.6721	Remote Similarity	NPD5224	Approved
0.672	Remote Similarity	NPD6011	Approved
0.6694	Remote Similarity	NPD7640	Approved
0.6694	Remote Similarity	NPD6008	Approved
0.6694	Remote Similarity	NPD7639	Approved
0.6694	Remote Similarity	NPD4700	Approved
0.6691	Remote Similarity	NPD8336	Approved
0.6691	Remote Similarity	NPD8337	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6639	Remote Similarity	NPD5223	Approved
0.6638	Remote Similarity	NPD4753	Phase 2
0.6637	Remote Similarity	NPD3666	Approved
0.6637	Remote Similarity	NPD3665	Phase 1
0.6637	Remote Similarity	NPD3133	Approved
0.6614	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5141	Approved
0.6594	Remote Similarity	NPD5956	Approved
0.6587	Remote Similarity	NPD4730	Approved
0.6587	Remote Similarity	NPD4729	Approved
0.6583	Remote Similarity	NPD4697	Phase 3
0.6562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.656	Remote Similarity	NPD4768	Approved
0.656	Remote Similarity	NPD4767	Approved
0.6552	Remote Similarity	NPD5737	Approved
0.6552	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6672	Approved
0.6525	Remote Similarity	NPD8034	Phase 2
0.6525	Remote Similarity	NPD8035	Phase 2
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.65	Remote Similarity	NPD4629	Approved
0.65	Remote Similarity	NPD8338	Approved
0.65	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD5210	Approved
0.6489	Remote Similarity	NPD6274	Approved
0.6484	Remote Similarity	NPD5250	Approved
0.6484	Remote Similarity	NPD5247	Approved
0.6484	Remote Similarity	NPD5249	Phase 3
0.6484	Remote Similarity	NPD5248	Approved
0.6484	Remote Similarity	NPD5251	Approved
0.6475	Remote Similarity	NPD5696	Approved
0.6475	Remote Similarity	NPD4225	Approved
0.6466	Remote Similarity	NPD7100	Approved
0.6466	Remote Similarity	NPD7101	Approved
0.6457	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5128	Approved
0.6441	Remote Similarity	NPD6698	Approved
0.6441	Remote Similarity	NPD46	Approved
0.641	Remote Similarity	NPD6903	Approved
0.64	Remote Similarity	NPD4754	Approved
0.6391	Remote Similarity	NPD6335	Approved
0.6379	Remote Similarity	NPD5279	Phase 3
0.6378	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6868	Approved
0.6357	Remote Similarity	NPD6371	Approved
0.6348	Remote Similarity	NPD3668	Phase 3
0.6341	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7524	Approved
0.6325	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD4223	Phase 3
0.6316	Remote Similarity	NPD4221	Approved
0.6316	Remote Similarity	NPD6317	Approved
0.6308	Remote Similarity	NPD5216	Approved
0.6308	Remote Similarity	NPD5215	Approved
0.6308	Remote Similarity	NPD5217	Approved
0.6293	Remote Similarity	NPD5329	Approved
0.6293	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD4695	Discontinued
0.6281	Remote Similarity	NPD5282	Discontinued
0.6269	Remote Similarity	NPD6314	Approved
0.6269	Remote Similarity	NPD6313	Approved
0.6267	Remote Similarity	NPD7625	Phase 1
0.626	Remote Similarity	NPD6053	Discontinued
0.6259	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6411	Approved
0.6239	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5135	Approved
0.6231	Remote Similarity	NPD5169	Approved
0.6231	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4522	Approved
0.6218	Remote Similarity	NPD6080	Approved
0.6218	Remote Similarity	NPD6673	Approved
0.6218	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD6904	Approved
0.6207	Remote Similarity	NPD4197	Approved
0.6202	Remote Similarity	NPD5168	Approved
0.6195	Remote Similarity	NPD7645	Phase 2
0.619	Remote Similarity	NPD7632	Discontinued

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