NPASS Compound

Structure

CID324875 OpenBabel06191716172D 63 70 0 0 1 0 0 0 0 0999 V2000 7.6845 -5.4225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0544 4.3045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 4.3045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0544 -2.3327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 -2.3327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7077 0.9859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8538 -1.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8538 -0.4930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8538 1.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8538 -1.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4153 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5615 0.4930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4153 2.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7077 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4153 1.9718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5615 0.4930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7077 2.9577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0998 -5.4225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4153 -3.9437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6845 -4.4366 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8538 1.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7077 1.9718 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2691 -4.4366 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0998 -4.4366 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7077 -0.9859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8538 0.4930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4153 -0.9859 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5383 -3.9437 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1230 -3.9437 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9536 -3.9437 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9536 -2.9577 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.0998 -2.4648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6845 -2.4648 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5383 -2.9577 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1230 -2.9577 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2459 -2.9577 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8306 -2.9577 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2691 -2.4648 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4153 0.9859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5615 3.4507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5615 -1.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7077 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8538 0.4930 0.0000 C 0 0 1 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 -2.5615 1.4789 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9536 -5.9155 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2691 -5.4225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3921 -4.4366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9768 -4.4366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8074 -4.4366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8074 -2.4648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0998 -1.4789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6845 -1.4789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4153 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2691 1.4789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4153 -2.9577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8306 -3.9437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2459 -3.9437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2691 -1.4789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3921 -2.4648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9768 -2.4648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 42 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 43 1 0 0 0 0 7 45 1 0 0 0 0 9 10 1 0 0 0 0 9 23 2 0 0 0 0 10 28 1 0 0 0 0 11 14 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 29 1 0 0 0 0 13 44 1 0 0 0 0 14 46 1 0 0 0 0 15 17 1 0 0 0 0 15 42 1 0 0 0 0 16 18 1 0 0 0 0 16 45 1 0 0 0 0 17 47 1 0 0 0 0 18 47 1 0 0 0 0 19 24 1 0 0 0 0 19 42 1 0 0 0 0 20 48 1 0 0 0 0 21 25 1 0 0 0 0 21 58 1 0 0 0 0 22 1 1 6 0 0 0 22 30 1 0 0 0 0 22 59 1 0 0 0 0 23 24 1 0 0 0 0 23 45 1 0 0 0 0 24 47 1 1 0 0 0 25 31 1 0 0 0 0 25 49 1 6 0 0 0 26 20 1 1 0 0 0 26 32 1 0 0 0 0 26 60 1 0 0 0 0 27 43 1 0 0 0 0 27 44 1 6 0 0 0 28 44 1 6 0 0 0 28 46 1 0 0 0 0 29 43 1 0 0 0 0 29 61 1 6 0 0 0 30 36 1 0 0 0 0 30 50 1 1 0 0 0 31 37 1 0 0 0 0 31 51 1 1 0 0 0 32 33 1 0 0 0 0 32 52 1 6 0 0 0 33 34 1 0 0 0 0 33 53 1 1 0 0 0 34 38 1 0 0 0 0 34 54 1 6 0 0 0 35 36 1 0 0 0 0 35 39 1 0 0 0 0 35 55 1 6 0 0 0 36 62 1 6 0 0 0 37 40 1 0 0 0 0 37 63 1 6 0 0 0 38 60 1 0 0 0 0 38 62 1 1 0 0 0 39 59 1 0 0 0 0 39 63 1 1 0 0 0 40 58 1 0 0 0 0 40 61 1 1 0 0 0 41 56 2 0 0 0 0 41 57 1 0 0 0 0 44 6 1 6 0 0 0 45 46 1 6 0 0 0 46 8 1 6 0 0 0 47 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	896.51
Volume:	888.387
LogP:	3.607
LogD:	3.45
LogS:	-3.842
# Rotatable Bonds:	8
TPSA:	254.52
# H-Bond Aceptor:	16
# H-Bond Donor:	9
# Rings:	8
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.125
Synthetic Accessibility Score:	6.181
Fsp3:	0.936
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:	-5.793
MDCK Permeability:	2.33030386880273e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.922
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.951

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	82.5777359008789%
Volume Distribution (VD):	0.313
Pgp-substrate:	11.173398971557617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.629
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.282
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.028

ADMET: Excretion

Clearance (CL):	0.725
Half-life (T1/2):	0.623

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.198
Drug-inuced Liver Injury (DILI):	0.011
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.037
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC324875

Natural Product ID:	NPC324875
*Common Name:**	(4As,6Ar,6As,6Br,8Ar,10S,12Ar,14Bs)-10-[(2S,3R,4S,5R)-3-[(2S,3R,4R,5S,6S)-3,5-Dihydroxy-6-Methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-4,5-Dihydroxyoxan-2-Yl]Oxy-2,2,6A,6B,9,9,12A-Heptamethyl-1,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydropicene-4A-Carboxylic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5R)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	OHJWWOZXCKEOGK-YLMYHLOISA-N
Standard InCHI:	InChI=1S/C47H76O16/c1-22-30(50)36(62-38-34(54)33(53)32(52)26(20-48)60-38)35(55)39(59-22)63-37-31(51)25(49)21-58-40(37)61-29-12-13-44(6)27(43(29,4)5)11-14-46(8)28(44)10-9-23-24-19-42(2,3)15-17-47(24,41(56)57)18-16-45(23,46)7/h9,22,24-40,48-55H,10-21H2,1-8H3,(H,56,57)/t22-,24-,25+,26+,27-,28+,29-,30-,31-,32+,33-,34+,35+,36+,37+,38-,39-,40-,44-,45+,46+,47-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)[C@H](O[C@H]3[C@@H](OC[C@H]([C@@H]3O)O)O[C@H]3CC[C@]4([C@H](C3(C)C)CC[C@@]3([C@@H]4CC=C4[C@@]3(C)CC[C@@]3([C@H]4CC(C)(C)CC3)C(=O)O)C)C)O[C@H]([C@@H]2O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2391934
PubChem CID:	73345902
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30520	Patrinia scabiosaefolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30520	Patrinia scabiosaefolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1083	Cell Line	A-375	Homo sapiens	IC50	=	5500.0	nM	PMID[480728]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	14700.0	nM	PMID[480728]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4600.0	nM	PMID[480728]

☑ 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 NPC324875 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	261
0.1-0.2	1737
0.2-0.3	5108
0.3-0.4	11934
0.4-0.5	10269
0.5-0.6	6164
0.6-0.7	3984
0.7-0.8	1930
0.8-0.85	607
0.85-0.9	291
0.9-0.95	169
0.95-1	243

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475516
1.0	High Similarity	NPC102439
1.0	High Similarity	NPC292677
1.0	High Similarity	NPC469946
1.0	High Similarity	NPC109079
1.0	High Similarity	NPC473373
1.0	High Similarity	NPC79718
1.0	High Similarity	NPC475504
1.0	High Similarity	NPC139044
1.0	High Similarity	NPC101744
1.0	High Similarity	NPC104071
1.0	High Similarity	NPC104400
1.0	High Similarity	NPC10320
1.0	High Similarity	NPC276093
1.0	High Similarity	NPC471383
1.0	High Similarity	NPC257468
0.9904	High Similarity	NPC166422
0.9904	High Similarity	NPC475467
0.9904	High Similarity	NPC309714
0.9904	High Similarity	NPC219180
0.9904	High Similarity	NPC134835
0.9904	High Similarity	NPC155410
0.9904	High Similarity	NPC473343
0.9904	High Similarity	NPC46665
0.9904	High Similarity	NPC475287
0.9904	High Similarity	NPC163183
0.9904	High Similarity	NPC174720
0.9904	High Similarity	NPC258885
0.9904	High Similarity	NPC96641
0.9904	High Similarity	NPC241909
0.9904	High Similarity	NPC150400
0.9904	High Similarity	NPC295823
0.9904	High Similarity	NPC114304
0.9904	High Similarity	NPC133818
0.9904	High Similarity	NPC192600
0.9904	High Similarity	NPC473826
0.9904	High Similarity	NPC151543
0.9904	High Similarity	NPC124296
0.9904	High Similarity	NPC73318
0.9904	High Similarity	NPC251263
0.9904	High Similarity	NPC323341
0.9904	High Similarity	NPC114287
0.9903	High Similarity	NPC164419
0.981	High Similarity	NPC70809
0.981	High Similarity	NPC161717
0.981	High Similarity	NPC261506
0.981	High Similarity	NPC67857
0.981	High Similarity	NPC471550
0.981	High Similarity	NPC471385
0.981	High Similarity	NPC469782
0.981	High Similarity	NPC294453
0.981	High Similarity	NPC100639
0.981	High Similarity	NPC204414
0.981	High Similarity	NPC473714
0.981	High Similarity	NPC79643
0.981	High Similarity	NPC76972
0.981	High Similarity	NPC305981
0.981	High Similarity	NPC250247
0.981	High Similarity	NPC54636
0.981	High Similarity	NPC65105
0.981	High Similarity	NPC119592
0.981	High Similarity	NPC476068
0.981	High Similarity	NPC298034
0.981	High Similarity	NPC57484
0.981	High Similarity	NPC224381
0.981	High Similarity	NPC202828
0.981	High Similarity	NPC60557
0.981	High Similarity	NPC227551
0.981	High Similarity	NPC309907
0.981	High Similarity	NPC4328
0.981	High Similarity	NPC123199
0.981	High Similarity	NPC43550
0.981	High Similarity	NPC475140
0.981	High Similarity	NPC236638
0.981	High Similarity	NPC475160
0.981	High Similarity	NPC475486
0.981	High Similarity	NPC293330
0.981	High Similarity	NPC41061
0.981	High Similarity	NPC164389
0.981	High Similarity	NPC71065
0.9808	High Similarity	NPC139894
0.9808	High Similarity	NPC473383
0.9806	High Similarity	NPC279554
0.9806	High Similarity	NPC174679
0.9806	High Similarity	NPC90856
0.9806	High Similarity	NPC474589
0.9806	High Similarity	NPC59804
0.9806	High Similarity	NPC270667
0.9806	High Similarity	NPC127056
0.9806	High Similarity	NPC475296
0.9806	High Similarity	NPC136877
0.9806	High Similarity	NPC29069
0.9806	High Similarity	NPC56713
0.9806	High Similarity	NPC164194
0.9717	High Similarity	NPC51465
0.9717	High Similarity	NPC476992
0.9717	High Similarity	NPC161674
0.9717	High Similarity	NPC160415
0.9717	High Similarity	NPC75287
0.9717	High Similarity	NPC288205
0.9717	High Similarity	NPC58448
0.9717	High Similarity	NPC26626
0.9717	High Similarity	NPC305267
0.9717	High Similarity	NPC37134
0.9717	High Similarity	NPC471384
0.9717	High Similarity	NPC291903
0.9712	High Similarity	NPC108748
0.9712	High Similarity	NPC473481
0.9712	High Similarity	NPC235841
0.9712	High Similarity	NPC211798
0.9712	High Similarity	NPC179434
0.9712	High Similarity	NPC297208
0.9712	High Similarity	NPC30397
0.9709	High Similarity	NPC204407
0.9709	High Similarity	NPC306746
0.9709	High Similarity	NPC237503
0.9709	High Similarity	NPC57362
0.9709	High Similarity	NPC167383
0.9626	High Similarity	NPC104137
0.9626	High Similarity	NPC300419
0.9626	High Similarity	NPC110633
0.9626	High Similarity	NPC69811
0.9626	High Similarity	NPC136768
0.9626	High Similarity	NPC191827
0.9626	High Similarity	NPC323359
0.9626	High Similarity	NPC148417
0.9626	High Similarity	NPC475119
0.9626	High Similarity	NPC123522
0.9626	High Similarity	NPC473452
0.9626	High Similarity	NPC475514
0.9626	High Similarity	NPC8524
0.9626	High Similarity	NPC68175
0.9626	High Similarity	NPC309223
0.9626	High Similarity	NPC102505
0.9626	High Similarity	NPC470876
0.9626	High Similarity	NPC33012
0.9626	High Similarity	NPC473824
0.9626	High Similarity	NPC475209
0.9626	High Similarity	NPC286457
0.9626	High Similarity	NPC220160
0.9626	High Similarity	NPC185466
0.9626	High Similarity	NPC471547
0.9626	High Similarity	NPC85154
0.9619	High Similarity	NPC128925
0.9619	High Similarity	NPC80843
0.9619	High Similarity	NPC1046
0.9619	High Similarity	NPC256798
0.9615	High Similarity	NPC476884
0.9615	High Similarity	NPC274507
0.9615	High Similarity	NPC199457
0.9615	High Similarity	NPC476882
0.9615	High Similarity	NPC68419
0.9615	High Similarity	NPC102914
0.9615	High Similarity	NPC476887
0.9615	High Similarity	NPC108709
0.9615	High Similarity	NPC78046
0.9615	High Similarity	NPC476886
0.9615	High Similarity	NPC476880
0.9615	High Similarity	NPC7870
0.9615	High Similarity	NPC476881
0.9615	High Similarity	NPC269095
0.9615	High Similarity	NPC476885
0.9615	High Similarity	NPC110139
0.9615	High Similarity	NPC476883
0.9615	High Similarity	NPC75747
0.9612	High Similarity	NPC284807
0.9612	High Similarity	NPC177246
0.9612	High Similarity	NPC28198
0.9612	High Similarity	NPC476123
0.9537	High Similarity	NPC471548
0.9537	High Similarity	NPC475899
0.9537	High Similarity	NPC109588
0.9537	High Similarity	NPC105800
0.9537	High Similarity	NPC237191
0.9537	High Similarity	NPC232237
0.9537	High Similarity	NPC36831
0.9537	High Similarity	NPC473459
0.9528	High Similarity	NPC475208
0.9528	High Similarity	NPC238935
0.9528	High Similarity	NPC189884
0.9528	High Similarity	NPC138334
0.9528	High Similarity	NPC204458
0.9528	High Similarity	NPC47063
0.9524	High Similarity	NPC31839
0.9524	High Similarity	NPC191763
0.9519	High Similarity	NPC127853
0.9519	High Similarity	NPC137917
0.9515	High Similarity	NPC283849
0.9515	High Similarity	NPC473538
0.945	High Similarity	NPC471577
0.945	High Similarity	NPC207738
0.945	High Similarity	NPC477464
0.945	High Similarity	NPC473401
0.945	High Similarity	NPC473386
0.945	High Similarity	NPC51564
0.945	High Similarity	NPC135849
0.945	High Similarity	NPC192791
0.945	High Similarity	NPC25663
0.9444	High Similarity	NPC473405
0.9444	High Similarity	NPC471580

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 NPC324875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	241
0.1-0.2	2042
0.2-0.3	3876
0.3-0.4	1952
0.4-0.5	598
0.5-0.6	266
0.6-0.7	142
0.7-0.8	21
0.8-0.85	8
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD8328	Phase 3
0.8796	High Similarity	NPD8132	Clinical (unspecified phase)
0.875	High Similarity	NPD8295	Clinical (unspecified phase)
0.8649	High Similarity	NPD8133	Approved
0.8108	Intermediate Similarity	NPD6412	Phase 2
0.8051	Intermediate Similarity	NPD8294	Approved
0.8051	Intermediate Similarity	NPD8377	Approved
0.8036	Intermediate Similarity	NPD6686	Approved
0.7983	Intermediate Similarity	NPD8335	Approved
0.7983	Intermediate Similarity	NPD8380	Approved
0.7983	Intermediate Similarity	NPD8379	Approved
0.7983	Intermediate Similarity	NPD8296	Approved
0.7983	Intermediate Similarity	NPD8378	Approved
0.7925	Intermediate Similarity	NPD7748	Approved
0.787	Intermediate Similarity	NPD7902	Approved
0.7869	Intermediate Similarity	NPD7507	Approved
0.7833	Intermediate Similarity	NPD8033	Approved
0.7736	Intermediate Similarity	NPD7515	Phase 2
0.7686	Intermediate Similarity	NPD8516	Approved
0.7686	Intermediate Similarity	NPD8513	Phase 3
0.7686	Intermediate Similarity	NPD8517	Approved
0.7686	Intermediate Similarity	NPD8515	Approved
0.768	Intermediate Similarity	NPD7319	Approved
0.76	Intermediate Similarity	NPD7736	Approved
0.7593	Intermediate Similarity	NPD7900	Approved
0.7593	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD7328	Approved
0.7583	Intermediate Similarity	NPD7327	Approved
0.7521	Intermediate Similarity	NPD7516	Approved
0.7456	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7503	Approved
0.7381	Intermediate Similarity	NPD8293	Discontinued
0.7248	Intermediate Similarity	NPD8034	Phase 2
0.7248	Intermediate Similarity	NPD8035	Phase 2
0.7227	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6370	Approved
0.7168	Intermediate Similarity	NPD7638	Approved
0.7167	Intermediate Similarity	NPD6882	Approved
0.7167	Intermediate Similarity	NPD8297	Approved
0.7105	Intermediate Similarity	NPD7639	Approved
0.7105	Intermediate Similarity	NPD7640	Approved
0.7087	Intermediate Similarity	NPD7492	Approved
0.7087	Intermediate Similarity	NPD7645	Phase 2
0.7073	Intermediate Similarity	NPD6009	Approved
0.7059	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6059	Approved
0.704	Intermediate Similarity	NPD6054	Approved
0.704	Intermediate Similarity	NPD6319	Approved
0.7031	Intermediate Similarity	NPD6616	Approved
0.7027	Intermediate Similarity	NPD6399	Phase 3
0.7027	Intermediate Similarity	NPD8171	Discontinued
0.7009	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6067	Discontinued
0.6977	Remote Similarity	NPD7078	Approved
0.6975	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD4632	Approved
0.6949	Remote Similarity	NPD6402	Approved
0.6949	Remote Similarity	NPD5739	Approved
0.6949	Remote Similarity	NPD6675	Approved
0.6949	Remote Similarity	NPD7128	Approved
0.6917	Remote Similarity	NPD6373	Approved
0.6917	Remote Similarity	NPD6372	Approved
0.686	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6016	Approved
0.685	Remote Similarity	NPD6015	Approved
0.6833	Remote Similarity	NPD6899	Approved
0.6833	Remote Similarity	NPD7320	Approved
0.6833	Remote Similarity	NPD6881	Approved
0.6803	Remote Similarity	NPD6649	Approved
0.6803	Remote Similarity	NPD8130	Phase 1
0.6803	Remote Similarity	NPD6650	Approved
0.68	Remote Similarity	NPD7115	Discovery
0.6797	Remote Similarity	NPD5988	Approved
0.6786	Remote Similarity	NPD6411	Approved
0.675	Remote Similarity	NPD5697	Approved
0.675	Remote Similarity	NPD5701	Approved
0.6721	Remote Similarity	NPD7290	Approved
0.6721	Remote Similarity	NPD6883	Approved
0.6721	Remote Similarity	NPD7102	Approved
0.6718	Remote Similarity	NPD8074	Phase 3
0.6696	Remote Similarity	NPD6698	Approved
0.6696	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD8450	Suspended
0.6667	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD6012	Approved
0.6639	Remote Similarity	NPD6013	Approved
0.6639	Remote Similarity	NPD6014	Approved
0.6638	Remote Similarity	NPD6084	Phase 2
0.6638	Remote Similarity	NPD6083	Phase 2
0.6636	Remote Similarity	NPD3618	Phase 1
0.6615	Remote Similarity	NPD7604	Phase 2
0.6612	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6101	Approved
0.6607	Remote Similarity	NPD5328	Approved
0.6606	Remote Similarity	NPD4786	Approved
0.6593	Remote Similarity	NPD8449	Approved
0.6589	Remote Similarity	NPD5983	Phase 2
0.6581	Remote Similarity	NPD4225	Approved
0.6577	Remote Similarity	NPD3573	Approved
0.6574	Remote Similarity	NPD3667	Approved
0.6557	Remote Similarity	NPD6011	Approved
0.6555	Remote Similarity	NPD7632	Discontinued
0.6541	Remote Similarity	NPD6033	Approved
0.6532	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6008	Approved
0.6515	Remote Similarity	NPD6336	Discontinued
0.6514	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3669	Approved
0.6496	Remote Similarity	NPD4755	Approved
0.6491	Remote Similarity	NPD7983	Approved
0.6491	Remote Similarity	NPD6079	Approved
0.6486	Remote Similarity	NPD7521	Approved
0.6486	Remote Similarity	NPD6409	Approved
0.6486	Remote Similarity	NPD7334	Approved
0.6486	Remote Similarity	NPD6684	Approved
0.6486	Remote Similarity	NPD7146	Approved
0.6486	Remote Similarity	NPD5330	Approved
0.6462	Remote Similarity	NPD6921	Approved
0.646	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6940	Discontinued
0.6452	Remote Similarity	NPD4634	Approved
0.6441	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4202	Approved
0.6435	Remote Similarity	NPD5779	Approved
0.6435	Remote Similarity	NPD5778	Approved
0.6389	Remote Similarity	NPD7525	Registered
0.6387	Remote Similarity	NPD5285	Approved
0.6387	Remote Similarity	NPD4696	Approved
0.6387	Remote Similarity	NPD5286	Approved
0.6387	Remote Similarity	NPD4700	Approved
0.6372	Remote Similarity	NPD6672	Approved
0.6372	Remote Similarity	NPD6903	Approved
0.6372	Remote Similarity	NPD5737	Approved
0.6355	Remote Similarity	NPD6114	Approved
0.6355	Remote Similarity	NPD6697	Approved
0.6355	Remote Similarity	NPD6115	Approved
0.6355	Remote Similarity	NPD6118	Approved
0.6345	Remote Similarity	NPD7625	Phase 1
0.633	Remote Similarity	NPD1779	Approved
0.633	Remote Similarity	NPD1780	Approved
0.6328	Remote Similarity	NPD6274	Approved
0.6325	Remote Similarity	NPD5695	Phase 3
0.6308	Remote Similarity	NPD7101	Approved
0.6308	Remote Similarity	NPD7100	Approved
0.6306	Remote Similarity	NPD3665	Phase 1
0.6306	Remote Similarity	NPD3666	Approved
0.6306	Remote Similarity	NPD3133	Approved
0.6303	Remote Similarity	NPD5696	Approved
0.6296	Remote Similarity	NPD8336	Approved
0.6296	Remote Similarity	NPD8337	Approved
0.6281	Remote Similarity	NPD5225	Approved
0.6281	Remote Similarity	NPD5226	Approved
0.6281	Remote Similarity	NPD4633	Approved
0.6281	Remote Similarity	NPD5211	Phase 2
0.6281	Remote Similarity	NPD5224	Approved
0.6279	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD4697	Phase 3
0.6271	Remote Similarity	NPD5221	Approved
0.6271	Remote Similarity	NPD5222	Approved
0.6262	Remote Similarity	NPD6116	Phase 1
0.626	Remote Similarity	NPD4768	Approved
0.626	Remote Similarity	NPD4767	Approved
0.6231	Remote Similarity	NPD6335	Approved
0.623	Remote Similarity	NPD5174	Approved
0.623	Remote Similarity	NPD5175	Approved
0.6222	Remote Similarity	NPD8448	Approved
0.6218	Remote Similarity	NPD5173	Approved
0.6212	Remote Similarity	NPD6909	Approved
0.6212	Remote Similarity	NPD6908	Approved
0.6204	Remote Similarity	NPD8391	Approved
0.6204	Remote Similarity	NPD8392	Approved
0.6204	Remote Similarity	NPD8390	Approved
0.6202	Remote Similarity	NPD6868	Approved
0.6198	Remote Similarity	NPD5223	Approved
0.6198	Remote Similarity	NPD5344	Discontinued
0.6194	Remote Similarity	NPD8342	Approved
0.6194	Remote Similarity	NPD8341	Approved
0.6194	Remote Similarity	NPD8299	Approved
0.6194	Remote Similarity	NPD8340	Approved
0.6186	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5141	Approved
0.6174	Remote Similarity	NPD4753	Phase 2
0.6168	Remote Similarity	NPD6117	Approved
0.6161	Remote Similarity	NPD3668	Phase 3
0.616	Remote Similarity	NPD4729	Approved
0.616	Remote Similarity	NPD4730	Approved
0.6154	Remote Similarity	NPD6317	Approved
0.6148	Remote Similarity	NPD8451	Approved
0.6134	Remote Similarity	NPD7614	Phase 1
0.6134	Remote Similarity	NPD7732	Phase 3
0.6134	Remote Similarity	NPD7839	Suspended
0.6121	Remote Similarity	NPD7838	Discovery
0.6119	Remote Similarity	NPD7830	Approved
0.6119	Remote Similarity	NPD7829	Approved
0.6115	Remote Similarity	NPD8338	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