NPASS Compound

Structure

CID270957 OpenBabel06191716072D 32 35 0 0 1 0 0 0 0 0999 V2000 -0.8477 3.4161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6914 1.0126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8466 2.4763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 3.4156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5368 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5366 0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5380 4.3913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3823 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8455 1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5369 0.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5374 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8463 -1.4648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2285 6.3422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6926 2.9280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6920 -0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3826 -0.9757 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6923 1.9523 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8460 0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8457 0.4886 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3831 4.8789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2287 7.3179 0.0000 C 0 0 0 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 1.6917 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8463 1.4642 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3834 5.8546 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2488 -1.4753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8656 -1.4769 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2279 4.3908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3839 7.8060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0739 7.8055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 7 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 22 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 23 1 0 0 0 0 14 27 1 0 0 0 0 15 1 1 1 0 0 0 15 18 1 0 0 0 0 16 25 1 1 0 0 0 17 28 1 1 0 0 0 18 26 1 6 0 0 0 19 24 1 0 0 0 0 19 26 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 6 0 0 0 21 24 1 0 0 0 0 21 29 1 6 0 0 0 22 27 2 3 0 0 0 22 30 1 0 0 0 0 23 31 2 0 0 0 0 23 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	449.31
Volume:	473.701
LogP:	3.117
LogD:	3.683
LogS:	-3.741
# Rotatable Bonds:	7
TPSA:	106.86
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.496
Synthetic Accessibility Score:	4.415
Fsp3:	0.923
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.212
MDCK Permeability:	1.69143113453174e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.854
Human Intestinal Absorption (HIA):	0.103
20% Bioavailability (F20%):	0.148
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.304
Plasma Protein Binding (PPB):	86.84932708740234%
Volume Distribution (VD):	0.398
Pgp-substrate:	10.771341323852539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.227
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.644
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.079
CYP3A4-substrate:	0.093

ADMET: Excretion

Clearance (CL):	6.115
Half-life (T1/2):	0.922

ADMET: Toxicity

hERG Blockers:	0.312
Human Hepatotoxicity (H-HT):	0.408
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.692
Skin Sensitization:	0.952
Carcinogencity:	0.225
Eye Corrosion:	0.029
Eye Irritation:	0.034
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC270957

Natural Product ID:	NPC270957
*Common Name:**	Glycochenodeoxycholic Acid
IUPAC Name:	2-[[(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetic acid
Synonyms:	Glycochenodeoxycholic acid; Glycoursodeoxycholate
Standard InCHIKey:	GHCZAUBVMUEKKP-XROMFQGDSA-N
Standard InCHI:	InChI=1S/C26H43NO5/c1-15(4-7-22(30)27-14-23(31)32)18-5-6-19-24-20(9-11-26(18,19)3)25(2)10-8-17(28)12-16(25)13-21(24)29/h15-21,24,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32)/t15-,16+,17-,18-,19+,20+,21+,24+,25+,26-/m1/s1
SMILES:	O[C@@H]1CC[C@]2([C@@H](C1)C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](CCC(=NCC(=O)O)O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL409348
PubChem CID:	12310288
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0001124] Glycinated bile acids and derivatives

*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

☑ 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
EC50	1
Others	5

Activity Type	# Activity
Individual Protein	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1631	Individual Protein	Solute carrier organic anion transporter family member 1A5	Rattus norvegicus	Km	=	5300.0	nM	PMID[480955]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	EC50	=	33900.0	nM	PMID[480953]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Efficacy	=	91.0	%	PMID[480953]
NPT27	Others	Unspecified		Activity	=	1.092	%	PMID[480954]
NPT27	Others	Unspecified		Activity	=	1.038	%	PMID[480954]
NPT754	Individual Protein	Ileal bile acid transporter	Homo sapiens	Km	=	4100.0	nM	PMID[480958]

☑ 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 NPC270957 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	126
0.1-0.2	1913
0.2-0.3	16986
0.3-0.4	11205
0.4-0.5	5556
0.5-0.6	5464
0.6-0.7	1258
0.7-0.8	178
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC171698
1.0	High Similarity	NPC119633
1.0	High Similarity	NPC321340
0.975	High Similarity	NPC175419
0.9625	High Similarity	NPC323180
0.9048	High Similarity	NPC323958
0.8022	Intermediate Similarity	NPC133995
0.8022	Intermediate Similarity	NPC159390
0.8022	Intermediate Similarity	NPC247891
0.7882	Intermediate Similarity	NPC171426
0.7882	Intermediate Similarity	NPC34046
0.7882	Intermediate Similarity	NPC80089
0.7882	Intermediate Similarity	NPC324700
0.7882	Intermediate Similarity	NPC224802
0.7816	Intermediate Similarity	NPC192456
0.7802	Intermediate Similarity	NPC283751
0.7791	Intermediate Similarity	NPC201276
0.7791	Intermediate Similarity	NPC220379
0.7791	Intermediate Similarity	NPC80891
0.7765	Intermediate Similarity	NPC212453
0.7692	Intermediate Similarity	NPC320478
0.7674	Intermediate Similarity	NPC471045
0.7647	Intermediate Similarity	NPC4209
0.7614	Intermediate Similarity	NPC73515
0.7586	Intermediate Similarity	NPC476176
0.7561	Intermediate Similarity	NPC66407
0.7558	Intermediate Similarity	NPC317913
0.7558	Intermediate Similarity	NPC207010
0.7529	Intermediate Similarity	NPC212733
0.7528	Intermediate Similarity	NPC154043
0.7528	Intermediate Similarity	NPC202688
0.7528	Intermediate Similarity	NPC60018
0.7528	Intermediate Similarity	NPC121121
0.747	Intermediate Similarity	NPC63588
0.747	Intermediate Similarity	NPC232925
0.747	Intermediate Similarity	NPC192192
0.747	Intermediate Similarity	NPC251201
0.7444	Intermediate Similarity	NPC111582
0.7444	Intermediate Similarity	NPC477285
0.7419	Intermediate Similarity	NPC317363
0.7416	Intermediate Similarity	NPC190940
0.7412	Intermediate Similarity	NPC167702
0.7412	Intermediate Similarity	NPC280026
0.7386	Intermediate Similarity	NPC320144
0.7381	Intermediate Similarity	NPC470071
0.7381	Intermediate Similarity	NPC127094
0.7381	Intermediate Similarity	NPC252182
0.7381	Intermediate Similarity	NPC1340
0.7381	Intermediate Similarity	NPC187471
0.7363	Intermediate Similarity	NPC473336
0.7363	Intermediate Similarity	NPC471044
0.7356	Intermediate Similarity	NPC143133
0.7356	Intermediate Similarity	NPC298168
0.7349	Intermediate Similarity	NPC477820
0.7349	Intermediate Similarity	NPC129829
0.7349	Intermediate Similarity	NPC254037
0.7333	Intermediate Similarity	NPC286719
0.7333	Intermediate Similarity	NPC477286
0.7326	Intermediate Similarity	NPC186851
0.7303	Intermediate Similarity	NPC477851
0.7294	Intermediate Similarity	NPC153719
0.7294	Intermediate Similarity	NPC470610
0.7283	Intermediate Similarity	NPC266651
0.7273	Intermediate Similarity	NPC185465
0.725	Intermediate Similarity	NPC114891
0.7222	Intermediate Similarity	NPC12933
0.7222	Intermediate Similarity	NPC109533
0.7222	Intermediate Similarity	NPC165396
0.7209	Intermediate Similarity	NPC48795
0.7209	Intermediate Similarity	NPC304499
0.7204	Intermediate Similarity	NPC302111
0.7204	Intermediate Similarity	NPC215968
0.7204	Intermediate Similarity	NPC155531
0.7204	Intermediate Similarity	NPC472272
0.7195	Intermediate Similarity	NPC142712
0.7184	Intermediate Similarity	NPC258130
0.7174	Intermediate Similarity	NPC299963
0.7159	Intermediate Similarity	NPC171658
0.7143	Intermediate Similarity	NPC30583
0.7143	Intermediate Similarity	NPC107919
0.7143	Intermediate Similarity	NPC289486
0.7143	Intermediate Similarity	NPC61107
0.7143	Intermediate Similarity	NPC472504
0.7126	Intermediate Similarity	NPC317242
0.7126	Intermediate Similarity	NPC158208
0.7126	Intermediate Similarity	NPC243027
0.7126	Intermediate Similarity	NPC196136
0.7125	Intermediate Similarity	NPC148174
0.7125	Intermediate Similarity	NPC71460
0.7125	Intermediate Similarity	NPC218585
0.7115	Intermediate Similarity	NPC478053
0.7111	Intermediate Similarity	NPC474714
0.7111	Intermediate Similarity	NPC261616
0.7108	Intermediate Similarity	NPC475884
0.7108	Intermediate Similarity	NPC48079
0.7108	Intermediate Similarity	NPC473230
0.7093	Intermediate Similarity	NPC232112
0.7091	Intermediate Similarity	NPC471121
0.7091	Intermediate Similarity	NPC471118
0.7079	Intermediate Similarity	NPC329117
0.7073	Intermediate Similarity	NPC41577
0.7073	Intermediate Similarity	NPC473276
0.7073	Intermediate Similarity	NPC474380
0.7065	Intermediate Similarity	NPC246956
0.7045	Intermediate Similarity	NPC163597
0.7045	Intermediate Similarity	NPC473916
0.7045	Intermediate Similarity	NPC477601
0.7045	Intermediate Similarity	NPC477602
0.7033	Intermediate Similarity	NPC469745
0.7033	Intermediate Similarity	NPC58631
0.7024	Intermediate Similarity	NPC472741
0.7021	Intermediate Similarity	NPC477283
0.7021	Intermediate Similarity	NPC103782
0.7021	Intermediate Similarity	NPC114378
0.7011	Intermediate Similarity	NPC10476
0.7011	Intermediate Similarity	NPC192501
0.7011	Intermediate Similarity	NPC228994
0.7	Intermediate Similarity	NPC477287
0.7	Intermediate Similarity	NPC471117
0.7	Intermediate Similarity	NPC471120
0.6988	Remote Similarity	NPC44122
0.6979	Remote Similarity	NPC24705
0.6979	Remote Similarity	NPC56962
0.6977	Remote Similarity	NPC109457
0.6977	Remote Similarity	NPC156277
0.6977	Remote Similarity	NPC157422
0.6977	Remote Similarity	NPC58057
0.6977	Remote Similarity	NPC478103
0.6977	Remote Similarity	NPC320549
0.6977	Remote Similarity	NPC151018
0.6977	Remote Similarity	NPC100586
0.6966	Remote Similarity	NPC192046
0.6966	Remote Similarity	NPC11907
0.6966	Remote Similarity	NPC477227
0.6966	Remote Similarity	NPC474574
0.6966	Remote Similarity	NPC133596
0.6966	Remote Similarity	NPC64081
0.6966	Remote Similarity	NPC105208
0.6966	Remote Similarity	NPC128951
0.6966	Remote Similarity	NPC185915
0.6966	Remote Similarity	NPC302578
0.6957	Remote Similarity	NPC2096
0.6957	Remote Similarity	NPC268040
0.6957	Remote Similarity	NPC208912
0.6951	Remote Similarity	NPC69149
0.6951	Remote Similarity	NPC159654
0.6951	Remote Similarity	NPC167995
0.6951	Remote Similarity	NPC118937
0.6951	Remote Similarity	NPC281540
0.6941	Remote Similarity	NPC252032
0.6941	Remote Similarity	NPC241085
0.6941	Remote Similarity	NPC469941
0.6941	Remote Similarity	NPC299948
0.6941	Remote Similarity	NPC470830
0.6941	Remote Similarity	NPC319671
0.6941	Remote Similarity	NPC476734
0.6932	Remote Similarity	NPC273366
0.6932	Remote Similarity	NPC478105
0.6932	Remote Similarity	NPC159789
0.6932	Remote Similarity	NPC231680
0.6932	Remote Similarity	NPC270306
0.6932	Remote Similarity	NPC91387
0.6932	Remote Similarity	NPC195155
0.6932	Remote Similarity	NPC97534
0.6932	Remote Similarity	NPC174964
0.6923	Remote Similarity	NPC470609
0.6923	Remote Similarity	NPC206735
0.6907	Remote Similarity	NPC77756
0.6907	Remote Similarity	NPC10274
0.6905	Remote Similarity	NPC476928
0.6889	Remote Similarity	NPC18857
0.6889	Remote Similarity	NPC147993
0.6889	Remote Similarity	NPC67657
0.6882	Remote Similarity	NPC5280
0.6882	Remote Similarity	NPC474284
0.6882	Remote Similarity	NPC474253
0.6882	Remote Similarity	NPC475820
0.6882	Remote Similarity	NPC474346
0.6882	Remote Similarity	NPC213737
0.6881	Remote Similarity	NPC106479
0.6875	Remote Similarity	NPC56777
0.6875	Remote Similarity	NPC160304
0.6875	Remote Similarity	NPC201607
0.686	Remote Similarity	NPC477929
0.686	Remote Similarity	NPC231945
0.686	Remote Similarity	NPC282454
0.6857	Remote Similarity	NPC36497
0.6854	Remote Similarity	NPC5767
0.6854	Remote Similarity	NPC472487
0.6854	Remote Similarity	NPC475742
0.6854	Remote Similarity	NPC472486
0.6848	Remote Similarity	NPC476071
0.6842	Remote Similarity	NPC2783
0.6842	Remote Similarity	NPC168231
0.6837	Remote Similarity	NPC219516
0.6837	Remote Similarity	NPC473066
0.6837	Remote Similarity	NPC52756
0.6829	Remote Similarity	NPC209686
0.6829	Remote Similarity	NPC249078
0.6829	Remote Similarity	NPC236099

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 NPC270957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	90
0.1-0.2	1639
0.2-0.3	4942
0.3-0.4	1739
0.4-0.5	417
0.5-0.6	260
0.6-0.7	44
0.7-0.8	16
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8298	Intermediate Similarity	NPD8418	Phase 2
0.8022	Intermediate Similarity	NPD6701	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD6700	Approved
0.7882	Intermediate Similarity	NPD6114	Approved
0.7882	Intermediate Similarity	NPD6118	Approved
0.7882	Intermediate Similarity	NPD6115	Approved
0.7882	Intermediate Similarity	NPD6697	Approved
0.7742	Intermediate Similarity	NPD6703	Approved
0.7742	Intermediate Similarity	NPD6702	Approved
0.7647	Intermediate Similarity	NPD6117	Approved
0.7558	Intermediate Similarity	NPD6116	Phase 1
0.7524	Intermediate Similarity	NPD8298	Phase 2
0.7412	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6705	Phase 1
0.6977	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3703	Phase 2
0.68	Remote Similarity	NPD7991	Discontinued
0.6744	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4787	Phase 1
0.6591	Remote Similarity	NPD6081	Approved
0.6574	Remote Similarity	NPD8174	Phase 2
0.6559	Remote Similarity	NPD6928	Phase 2
0.6495	Remote Similarity	NPD8308	Discontinued
0.6489	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD4789	Approved
0.6477	Remote Similarity	NPD4245	Approved
0.6477	Remote Similarity	NPD4244	Approved
0.6437	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5360	Phase 3
0.6395	Remote Similarity	NPD4224	Phase 2
0.6383	Remote Similarity	NPD7525	Registered
0.6364	Remote Similarity	NPD3698	Phase 2
0.6346	Remote Similarity	NPD7919	Phase 3
0.6346	Remote Similarity	NPD7920	Phase 3
0.6337	Remote Similarity	NPD8035	Phase 2
0.6337	Remote Similarity	NPD8034	Phase 2
0.6286	Remote Similarity	NPD7638	Approved
0.6286	Remote Similarity	NPD8088	Phase 1
0.6279	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6920	Discontinued
0.6237	Remote Similarity	NPD8144	Approved
0.6237	Remote Similarity	NPD8143	Approved
0.6226	Remote Similarity	NPD7639	Approved
0.6226	Remote Similarity	NPD7640	Approved
0.6222	Remote Similarity	NPD5777	Approved
0.6196	Remote Similarity	NPD3702	Approved
0.617	Remote Similarity	NPD3671	Phase 1
0.6111	Remote Similarity	NPD7632	Discontinued
0.6105	Remote Similarity	NPD5354	Approved
0.6055	Remote Similarity	NPD7986	Approved
0.6055	Remote Similarity	NPD7912	Approved
0.6055	Remote Similarity	NPD7987	Approved
0.6055	Remote Similarity	NPD7911	Approved
0.605	Remote Similarity	NPD6908	Approved
0.605	Remote Similarity	NPD6909	Approved
0.6044	Remote Similarity	NPD4758	Discontinued
0.6034	Remote Similarity	NPD7755	Approved
0.6034	Remote Similarity	NPD7754	Approved
0.6	Remote Similarity	NPD5364	Discontinued
0.6	Remote Similarity	NPD4777	Suspended
0.6	Remote Similarity	NPD4776	Phase 2
0.5982	Remote Similarity	NPD6415	Discontinued
0.5962	Remote Similarity	NPD8171	Discontinued
0.5946	Remote Similarity	NPD8040	Discontinued
0.5897	Remote Similarity	NPD6940	Discontinued
0.5893	Remote Similarity	NPD7989	Approved
0.5893	Remote Similarity	NPD7990	Approved
0.587	Remote Similarity	NPD3187	Discontinued
0.5865	Remote Similarity	NPD7515	Phase 2
0.5851	Remote Similarity	NPD7339	Approved
0.5851	Remote Similarity	NPD6942	Approved
0.5843	Remote Similarity	NPD2263	Discontinued
0.5825	Remote Similarity	NPD5328	Approved
0.581	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6399	Phase 3
0.58	Remote Similarity	NPD4786	Approved
0.578	Remote Similarity	NPD6404	Discontinued
0.5755	Remote Similarity	NPD5771	Approved
0.5728	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD6333	Approved
0.5725	Remote Similarity	NPD6334	Approved
0.5714	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6079	Approved
0.57	Remote Similarity	NPD4788	Approved
0.5686	Remote Similarity	NPD3618	Phase 1
0.567	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.567	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6402	Approved
0.5664	Remote Similarity	NPD7128	Approved
0.5664	Remote Similarity	NPD6675	Approved
0.5664	Remote Similarity	NPD5739	Approved
0.5652	Remote Similarity	NPD3725	Approved
0.5652	Remote Similarity	NPD3726	Approved
0.5641	Remote Similarity	NPD8077	Approved
0.5641	Remote Similarity	NPD8078	Approved
0.5625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD7645	Phase 2
0.5607	Remote Similarity	NPD5707	Approved
0.5607	Remote Similarity	NPD7748	Approved
0.56	Remote Similarity	NPD3667	Approved
0.56	Remote Similarity	NPD7345	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