NPASS Compound

Structure

CID224802 OpenBabel06191716022D 31 34 0 0 1 0 0 0 0 0999 V2000 1.3338 -2.3086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9677 4.5542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0983 5.8084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8462 3.4502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 1.9877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 -1.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5350 2.4384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5348 1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3792 0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 2.4394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5345 1.4645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6191 4.2022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5351 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 3.9015 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8224 5.1556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3795 0.0010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8453 -0.4877 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6912 2.9266 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8456 1.4636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8448 1.4641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6903 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9759 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7497 5.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 2.4389 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6901 0.9764 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2457 -0.4987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8659 -0.5003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9530 6.4098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4738 4.8036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 27 1 0 0 0 0 12 26 1 0 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 2 1 1 0 0 0 15 19 1 0 0 0 0 16 3 1 1 0 0 0 16 25 1 0 0 0 0 17 28 1 1 0 0 0 18 6 1 1 0 0 0 18 22 1 0 0 0 0 18 24 1 0 0 0 0 19 26 1 6 0 0 0 20 23 1 0 0 0 0 20 26 1 6 0 0 0 21 23 1 0 0 0 0 21 27 1 6 0 0 0 22 27 1 1 0 0 0 23 24 1 0 0 0 0 24 29 1 0 0 0 0 25 30 2 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.34
Volume:	473.847
LogP:	5.506
LogD:	5.371
LogS:	-4.459
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.544
Synthetic Accessibility Score:	4.766
Fsp3:	0.963
Lipinski Rule-of-5:	Accepted
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:	-4.855
MDCK Permeability:	5.27685770066455e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.576
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.187

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.232
Plasma Protein Binding (PPB):	97.06524658203125%
Volume Distribution (VD):	0.874
Pgp-substrate:	1.6930969953536987%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.427
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.592
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	6.722
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.358
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.053
Skin Sensitization:	0.945
Carcinogencity:	0.112
Eye Corrosion:	0.943
Eye Irritation:	0.461
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC224802

Natural Product ID:	NPC224802
*Common Name:**	Bile Acid
IUPAC Name:	(2S,4R)-4-[(3R,5S,6R,7R,8S,9S,10S,13R,14S,17R)-6-ethyl-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]-2-methylpentanoic acid
Synonyms:	Bile Acid
Standard InCHIKey:	HSINOMROUCMIEA-FGVHQWLLSA-N
Standard InCHI:	InChI=1S/C27H46O4/c1-6-18-22-14-17(28)9-11-27(22,5)21-10-12-26(4)19(15(2)13-16(3)25(30)31)7-8-20(26)23(21)24(18)29/h15-24,28-29H,6-14H2,1-5H3,(H,30,31)/t15-,16+,17-,18-,19-,20+,21+,22+,23+,24-,26-,27-/m1/s1
SMILES:	CC[C@H]1[C@@H](O)[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2([C@H]1C[C@H](O)CC2)C)[C@@H](C[C@@H](C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1258080
PubChem CID:	17755104
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:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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
NPO30797	Fel serpentis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30916	Fel gallus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO6070	Fel serpentis liquidum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO15894	Fel gallus domesticus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3948	Individual Protein	G-protein coupled bile acid receptor 1	Mus musculus	IC50	=	250.0	nM	PMID[517939]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	IC50	=	140.0	nM	PMID[517939]

☑ 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 NPC224802 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	330
0.1-0.2	2883
0.2-0.3	10554
0.3-0.4	13007
0.4-0.5	5748
0.5-0.6	4764
0.6-0.7	3875
0.7-0.8	1264
0.8-0.85	168
0.85-0.9	77
0.9-0.95	14
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC171426
1.0	High Similarity	NPC324700
1.0	High Similarity	NPC34046
1.0	High Similarity	NPC80089
0.9863	High Similarity	NPC201276
0.9863	High Similarity	NPC80891
0.9722	High Similarity	NPC4209
0.9589	High Similarity	NPC207010
0.9589	High Similarity	NPC317913
0.9583	High Similarity	NPC212733
0.9474	High Similarity	NPC121121
0.9444	High Similarity	NPC280026
0.9444	High Similarity	NPC167702
0.9333	High Similarity	NPC320144
0.9324	High Similarity	NPC143133
0.9324	High Similarity	NPC298168
0.9231	High Similarity	NPC473336
0.9231	High Similarity	NPC471044
0.9211	High Similarity	NPC477851
0.92	High Similarity	NPC185465
0.9091	High Similarity	NPC12933
0.9041	High Similarity	NPC232112
0.9	High Similarity	NPC472272
0.9	High Similarity	NPC302111
0.8974	High Similarity	NPC61107
0.8974	High Similarity	NPC30583
0.8974	High Similarity	NPC289486
0.8961	High Similarity	NPC261616
0.8947	High Similarity	NPC329117
0.8904	High Similarity	NPC320549
0.8904	High Similarity	NPC156277
0.8904	High Similarity	NPC58057
0.8904	High Similarity	NPC151018
0.8889	High Similarity	NPC476734
0.8889	High Similarity	NPC319671
0.8889	High Similarity	NPC469941
0.8889	High Similarity	NPC252032
0.8846	High Similarity	NPC58631
0.8846	High Similarity	NPC469745
0.88	High Similarity	NPC195155
0.88	High Similarity	NPC174964
0.88	High Similarity	NPC273366
0.88	High Similarity	NPC159789
0.88	High Similarity	NPC97534
0.8767	High Similarity	NPC477929
0.8734	High Similarity	NPC268040
0.8718	High Similarity	NPC470609
0.8684	High Similarity	NPC5767
0.8684	High Similarity	NPC472487
0.8684	High Similarity	NPC475742
0.8684	High Similarity	NPC472486
0.8675	High Similarity	NPC56962
0.8675	High Similarity	NPC24705
0.8667	High Similarity	NPC254340
0.8667	High Similarity	NPC477930
0.8649	High Similarity	NPC469940
0.8649	High Similarity	NPC89310
0.863	High Similarity	NPC327728
0.863	High Similarity	NPC131892
0.863	High Similarity	NPC213178
0.863	High Similarity	NPC6120
0.863	High Similarity	NPC196197
0.8608	High Similarity	NPC476071
0.859	High Similarity	NPC220379
0.8571	High Similarity	NPC221420
0.8571	High Similarity	NPC180199
0.8571	High Similarity	NPC77756
0.8571	High Similarity	NPC475031
0.8571	High Similarity	NPC212453
0.8571	High Similarity	NPC477919
0.8571	High Similarity	NPC23884
0.8553	High Similarity	NPC125767
0.8553	High Similarity	NPC472311
0.8553	High Similarity	NPC21220
0.8537	High Similarity	NPC2783
0.8519	High Similarity	NPC50438
0.8519	High Similarity	NPC473299
0.8519	High Similarity	NPC319909
0.8514	High Similarity	NPC477850
0.8472	Intermediate Similarity	NPC268736
0.8472	Intermediate Similarity	NPC42060
0.8472	Intermediate Similarity	NPC477931
0.8471	Intermediate Similarity	NPC52756
0.8462	Intermediate Similarity	NPC476732
0.8462	Intermediate Similarity	NPC472608
0.8462	Intermediate Similarity	NPC471045
0.8462	Intermediate Similarity	NPC199965
0.8442	Intermediate Similarity	NPC477932
0.8442	Intermediate Similarity	NPC477933
0.8434	Intermediate Similarity	NPC264005
0.8434	Intermediate Similarity	NPC269360
0.8434	Intermediate Similarity	NPC252714
0.8434	Intermediate Similarity	NPC33768
0.8415	Intermediate Similarity	NPC264317
0.8415	Intermediate Similarity	NPC294438
0.8378	Intermediate Similarity	NPC66407
0.8378	Intermediate Similarity	NPC64466
0.8375	Intermediate Similarity	NPC73515
0.8372	Intermediate Similarity	NPC291373
0.8372	Intermediate Similarity	NPC244356
0.8372	Intermediate Similarity	NPC224060
0.8372	Intermediate Similarity	NPC476189
0.8354	Intermediate Similarity	NPC476176
0.8333	Intermediate Similarity	NPC477918
0.8333	Intermediate Similarity	NPC16377
0.8333	Intermediate Similarity	NPC474719
0.8313	Intermediate Similarity	NPC476727
0.8313	Intermediate Similarity	NPC12774
0.8313	Intermediate Similarity	NPC476726
0.8313	Intermediate Similarity	NPC80700
0.8312	Intermediate Similarity	NPC477934
0.8293	Intermediate Similarity	NPC237938
0.8293	Intermediate Similarity	NPC219535
0.8289	Intermediate Similarity	NPC310766
0.8276	Intermediate Similarity	NPC277399
0.8272	Intermediate Similarity	NPC154043
0.8272	Intermediate Similarity	NPC164289
0.8272	Intermediate Similarity	NPC202688
0.8272	Intermediate Similarity	NPC242771
0.8272	Intermediate Similarity	NPC100366
0.8272	Intermediate Similarity	NPC60018
0.8272	Intermediate Similarity	NPC311642
0.8267	Intermediate Similarity	NPC251201
0.8267	Intermediate Similarity	NPC108131
0.8267	Intermediate Similarity	NPC63588
0.8267	Intermediate Similarity	NPC232925
0.8267	Intermediate Similarity	NPC192192
0.8235	Intermediate Similarity	NPC213832
0.8235	Intermediate Similarity	NPC220498
0.8235	Intermediate Similarity	NPC57954
0.8228	Intermediate Similarity	NPC31031
0.8228	Intermediate Similarity	NPC243594
0.8228	Intermediate Similarity	NPC26029
0.8214	Intermediate Similarity	NPC263802
0.8214	Intermediate Similarity	NPC239938
0.8214	Intermediate Similarity	NPC202937
0.8205	Intermediate Similarity	NPC471046
0.8193	Intermediate Similarity	NPC131350
0.8193	Intermediate Similarity	NPC473350
0.8182	Intermediate Similarity	NPC62407
0.8182	Intermediate Similarity	NPC279974
0.8182	Intermediate Similarity	NPC133922
0.8182	Intermediate Similarity	NPC287354
0.8182	Intermediate Similarity	NPC263135
0.8182	Intermediate Similarity	NPC288906
0.8171	Intermediate Similarity	NPC111582
0.8171	Intermediate Similarity	NPC477285
0.8171	Intermediate Similarity	NPC327451
0.8171	Intermediate Similarity	NPC471037
0.8158	Intermediate Similarity	NPC1340
0.8158	Intermediate Similarity	NPC127094
0.8158	Intermediate Similarity	NPC470071
0.8158	Intermediate Similarity	NPC252182
0.8158	Intermediate Similarity	NPC187471
0.8148	Intermediate Similarity	NPC48756
0.8148	Intermediate Similarity	NPC280781
0.8148	Intermediate Similarity	NPC190940
0.814	Intermediate Similarity	NPC169933
0.8133	Intermediate Similarity	NPC129829
0.8133	Intermediate Similarity	NPC254037
0.8133	Intermediate Similarity	NPC324607
0.8133	Intermediate Similarity	NPC474962
0.8133	Intermediate Similarity	NPC321732
0.8133	Intermediate Similarity	NPC477820
0.8125	Intermediate Similarity	NPC472310
0.8118	Intermediate Similarity	NPC146937
0.8118	Intermediate Similarity	NPC4309
0.8118	Intermediate Similarity	NPC471900
0.8108	Intermediate Similarity	NPC474221
0.8108	Intermediate Similarity	NPC130459
0.8108	Intermediate Similarity	NPC41542
0.8108	Intermediate Similarity	NPC478180
0.8101	Intermediate Similarity	NPC474404
0.8101	Intermediate Similarity	NPC471151
0.8101	Intermediate Similarity	NPC264602
0.8095	Intermediate Similarity	NPC83242
0.809	Intermediate Similarity	NPC116683
0.809	Intermediate Similarity	NPC234564
0.8082	Intermediate Similarity	NPC230047
0.8082	Intermediate Similarity	NPC19311
0.8077	Intermediate Similarity	NPC186851
0.8072	Intermediate Similarity	NPC477434
0.8068	Intermediate Similarity	NPC47853
0.8056	Intermediate Similarity	NPC114891
0.8052	Intermediate Similarity	NPC477229
0.8052	Intermediate Similarity	NPC282905
0.8052	Intermediate Similarity	NPC470610
0.8052	Intermediate Similarity	NPC68426
0.8052	Intermediate Similarity	NPC153719
0.8049	Intermediate Similarity	NPC317066
0.8049	Intermediate Similarity	NPC13494
0.8049	Intermediate Similarity	NPC148740
0.8049	Intermediate Similarity	NPC477935
0.8049	Intermediate Similarity	NPC328007
0.8049	Intermediate Similarity	NPC286719
0.8049	Intermediate Similarity	NPC477286
0.8049	Intermediate Similarity	NPC102156
0.8046	Intermediate Similarity	NPC211403
0.8046	Intermediate Similarity	NPC198242
0.8025	Intermediate Similarity	NPC472853

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 NPC224802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	3298
0.2-0.3	3608
0.3-0.4	1152
0.4-0.5	321
0.5-0.6	198
0.6-0.7	174
0.7-0.8	17
0.8-0.85	14
0.85-0.9	5
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6114	Approved
1.0	High Similarity	NPD6118	Approved
1.0	High Similarity	NPD6115	Approved
1.0	High Similarity	NPD6697	Approved
0.9722	High Similarity	NPD6117	Approved
0.9589	High Similarity	NPD6116	Phase 1
0.9444	High Similarity	NPD6113	Clinical (unspecified phase)
0.8904	High Similarity	NPD4808	Clinical (unspecified phase)
0.8904	High Similarity	NPD4809	Clinical (unspecified phase)
0.88	High Similarity	NPD3703	Phase 2
0.863	High Similarity	NPD3699	Clinical (unspecified phase)
0.863	High Similarity	NPD3700	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD6081	Approved
0.8267	Intermediate Similarity	NPD4245	Approved
0.8267	Intermediate Similarity	NPD4789	Approved
0.8267	Intermediate Similarity	NPD4244	Approved
0.8243	Intermediate Similarity	NPD5360	Phase 3
0.8243	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD4224	Phase 2
0.8133	Intermediate Similarity	NPD3698	Phase 2
0.8082	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD5777	Approved
0.7895	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3702	Approved
0.7841	Intermediate Similarity	NPD8035	Phase 2
0.7841	Intermediate Similarity	NPD8034	Phase 2
0.7826	Intermediate Similarity	NPD8418	Phase 2
0.7778	Intermediate Similarity	NPD3671	Phase 1
0.7692	Intermediate Similarity	NPD4758	Discontinued
0.7561	Intermediate Similarity	NPD5364	Discontinued
0.7342	Intermediate Similarity	NPD4787	Phase 1
0.734	Intermediate Similarity	NPD7638	Approved
0.7263	Intermediate Similarity	NPD7640	Approved
0.7263	Intermediate Similarity	NPD7639	Approved
0.7253	Intermediate Similarity	NPD7515	Phase 2
0.7241	Intermediate Similarity	NPD4786	Approved
0.7222	Intermediate Similarity	NPD5328	Approved
0.7176	Intermediate Similarity	NPD6928	Phase 2
0.7174	Intermediate Similarity	NPD6399	Phase 3
0.7162	Intermediate Similarity	NPD3198	Approved
0.7126	Intermediate Similarity	NPD4788	Approved
0.7113	Intermediate Similarity	NPD7632	Discontinued
0.7079	Intermediate Similarity	NPD3618	Phase 1
0.7065	Intermediate Similarity	NPD6079	Approved
0.7011	Intermediate Similarity	NPD3667	Approved
0.6977	Remote Similarity	NPD7525	Registered
0.697	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7748	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD6675	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6402	Approved
0.6809	Remote Similarity	NPD4202	Approved
0.6771	Remote Similarity	NPD4697	Phase 3
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6765	Remote Similarity	NPD6881	Approved
0.6762	Remote Similarity	NPD8298	Phase 2
0.6701	Remote Similarity	NPD7902	Approved
0.6701	Remote Similarity	NPD4755	Approved
0.6701	Remote Similarity	NPD6083	Phase 2
0.6701	Remote Similarity	NPD5173	Approved
0.6701	Remote Similarity	NPD6084	Phase 2
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6636	Remote Similarity	NPD6940	Discontinued
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6604	Remote Similarity	NPD4632	Approved
0.6604	Remote Similarity	NPD8133	Approved
0.6602	Remote Similarity	NPD6011	Approved
0.6596	Remote Similarity	NPD6700	Approved
0.6596	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7909	Approved
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6617	Approved
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6566	Remote Similarity	NPD5286	Approved
0.6566	Remote Similarity	NPD4700	Approved
0.6566	Remote Similarity	NPD5285	Approved
0.6566	Remote Similarity	NPD4696	Approved
0.6559	Remote Similarity	NPD5737	Approved
0.6559	Remote Similarity	NPD6672	Approved
0.6559	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4238	Approved
0.6552	Remote Similarity	NPD4802	Phase 2
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6526	Remote Similarity	NPD6703	Approved
0.6526	Remote Similarity	NPD6702	Approved
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6509	Remote Similarity	NPD8297	Approved
0.6509	Remote Similarity	NPD6882	Approved
0.65	Remote Similarity	NPD5223	Approved
0.65	Remote Similarity	NPD1700	Approved
0.6489	Remote Similarity	NPD4753	Phase 2
0.6484	Remote Similarity	NPD3668	Phase 3
0.6458	Remote Similarity	NPD8171	Discontinued
0.6442	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5226	Approved
0.6436	Remote Similarity	NPD5211	Phase 2
0.6436	Remote Similarity	NPD4633	Approved
0.6436	Remote Similarity	NPD5225	Approved
0.6436	Remote Similarity	NPD5224	Approved
0.6422	Remote Similarity	NPD6009	Approved
0.6408	Remote Similarity	NPD6920	Discontinued
0.6408	Remote Similarity	NPD6008	Approved
0.6395	Remote Similarity	NPD6942	Approved
0.6395	Remote Similarity	NPD7339	Approved
0.6392	Remote Similarity	NPD7900	Approved
0.6392	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD6903	Approved
0.6381	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5175	Approved
0.6373	Remote Similarity	NPD4754	Approved
0.6373	Remote Similarity	NPD5174	Approved
0.6364	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3617	Approved
0.6344	Remote Similarity	NPD5279	Phase 3
0.6344	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6868	Approved
0.6327	Remote Similarity	NPD5695	Phase 3
0.6327	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4634	Approved
0.6311	Remote Similarity	NPD5141	Approved
0.63	Remote Similarity	NPD5696	Approved
0.6273	Remote Similarity	NPD7115	Discovery
0.6267	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD6705	Phase 1
0.6264	Remote Similarity	NPD4221	Approved
0.6264	Remote Similarity	NPD4223	Phase 3
0.6261	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD4768	Approved
0.6237	Remote Similarity	NPD5329	Approved
0.6228	Remote Similarity	NPD7604	Phase 2
0.6216	Remote Similarity	NPD6335	Approved
0.6196	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD3669	Approved
0.6195	Remote Similarity	NPD5983	Phase 2
0.619	Remote Similarity	NPD6412	Phase 2
0.6186	Remote Similarity	NPD5281	Approved
0.6186	Remote Similarity	NPD7637	Suspended
0.6186	Remote Similarity	NPD5284	Approved
0.6182	Remote Similarity	NPD6274	Approved
0.6174	Remote Similarity	NPD7492	Approved
0.617	Remote Similarity	NPD6098	Approved
0.6168	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD7991	Discontinued
0.6162	Remote Similarity	NPD5210	Approved
0.6162	Remote Similarity	NPD4629	Approved
0.6161	Remote Similarity	NPD7101	Approved
0.6161	Remote Similarity	NPD7100	Approved
0.6154	Remote Similarity	NPD1780	Approved
0.6154	Remote Similarity	NPD4139	Approved
0.6154	Remote Similarity	NPD1779	Approved
0.6154	Remote Similarity	NPD4692	Approved
0.6154	Remote Similarity	NPD7736	Approved
0.6146	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6904	Approved
0.6146	Remote Similarity	NPD6673	Approved
0.6146	Remote Similarity	NPD6080	Approved
0.6136	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4729	Approved
0.6132	Remote Similarity	NPD5168	Approved
0.6132	Remote Similarity	NPD6415	Discontinued
0.6132	Remote Similarity	NPD4730	Approved
0.6132	Remote Similarity	NPD5128	Approved
0.6129	Remote Similarity	NPD4197	Approved
0.6126	Remote Similarity	NPD6317	Approved
0.6126	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6616	Approved
0.6121	Remote Similarity	NPD6336	Discontinued
0.6111	Remote Similarity	NPD7645	Phase 2
0.6106	Remote Similarity	NPD6059	Approved
0.6106	Remote Similarity	NPD6054	Approved
0.6102	Remote Similarity	NPD7319	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