NPASS Compound

Structure

CID317913 OpenBabel06191716142D 28 31 0 0 1 0 0 0 0 0999 V2000 -2.5310 3.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5298 2.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2153 3.4037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2144 1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2142 0.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2156 4.3761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6849 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 1.4593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8423 0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6866 1.9458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8429 -1.4599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6858 -0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3730 2.9177 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6852 -0.9729 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6861 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3727 1.9453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5293 0.4860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8432 0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9734 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8426 -1.4604 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0579 4.8621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5295 1.4588 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 2.5514 -1.4726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8423 -2.4604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0581 5.8345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8999 4.3756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 7 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 22 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 1 1 1 0 0 0 14 17 1 0 0 0 0 15 25 1 1 0 0 0 16 13 1 1 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 23 1 6 0 0 0 18 23 1 6 0 0 0 19 24 1 6 0 0 0 20 21 1 0 0 0 0 20 24 1 1 0 0 0 21 26 1 6 0 0 0 22 27 2 0 0 0 0 22 28 1 0 0 0 0 23 2 1 6 0 0 0 24 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.29
Volume:	421.959
LogP:	4.463
LogD:	4.379
LogS:	-4.272
# Rotatable Bonds:	4
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.659
Synthetic Accessibility Score:	4.35
Fsp3:	0.958
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:	-5.137
MDCK Permeability:	1.9231694750487804e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.652
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.543

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.162
Plasma Protein Binding (PPB):	96.29130554199219%
Volume Distribution (VD):	0.594
Pgp-substrate:	2.15857195854187%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.385
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.211
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	2.917
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.347
Human Hepatotoxicity (H-HT):	0.404
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.125
Skin Sensitization:	0.963
Carcinogencity:	0.049
Eye Corrosion:	0.539
Eye Irritation:	0.872
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC317913

Natural Product ID:	NPC317913
*Common Name:**	Murocholic Acid
IUPAC Name:	(4R)-4-[(3R,5R,6R,8S,9S,10R,13R,14S,17R)-3,6-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]pentanoic acid
Synonyms:	Murocholic Acid
Standard InCHIKey:	DGABKXLVXPYZII-PLYQRAMGSA-N
Standard InCHI:	InChI=1S/C24H40O4/c1-14(4-7-22(27)28)17-5-6-18-16-13-21(26)20-12-15(25)8-10-24(20,3)19(16)9-11-23(17,18)2/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17-,18+,19+,20+,21-,23-,24-/m1/s1
SMILES:	CC(CCC(=O)O)C1CCC2C1(CCC3C2CC(C4C3(CCC(C4)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL272620
PubChem CID:	5283821
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

☑ 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	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	EC50	=	4890.0	nM	PMID[489632]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Efficacy	=	94.4	%	PMID[489632]

☑ 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 NPC317913 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	320
0.1-0.2	2898
0.2-0.3	11643
0.3-0.4	12047
0.4-0.5	5761
0.5-0.6	4734
0.6-0.7	3749
0.7-0.8	1293
0.8-0.85	154
0.85-0.9	66
0.9-0.95	20
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC207010
0.9859	High Similarity	NPC4209
0.9718	High Similarity	NPC212733
0.9589	High Similarity	NPC224802
0.9589	High Similarity	NPC324700
0.9589	High Similarity	NPC80089
0.9589	High Similarity	NPC34046
0.9589	High Similarity	NPC171426
0.9577	High Similarity	NPC167702
0.9577	High Similarity	NPC280026
0.9459	High Similarity	NPC80891
0.9459	High Similarity	NPC201276
0.9459	High Similarity	NPC320144
0.9452	High Similarity	NPC143133
0.9452	High Similarity	NPC298168
0.9342	High Similarity	NPC121121
0.9324	High Similarity	NPC185465
0.9211	High Similarity	NPC12933
0.9167	High Similarity	NPC232112
0.9091	High Similarity	NPC289486
0.9091	High Similarity	NPC30583
0.9091	High Similarity	NPC61107
0.9079	High Similarity	NPC261616
0.9067	High Similarity	NPC329117
0.9028	High Similarity	NPC151018
0.9028	High Similarity	NPC320549
0.9028	High Similarity	NPC58057
0.9028	High Similarity	NPC156277
0.9014	High Similarity	NPC469941
0.9014	High Similarity	NPC252032
0.9014	High Similarity	NPC476734
0.9014	High Similarity	NPC319671
0.8961	High Similarity	NPC58631
0.8933	High Similarity	NPC475031
0.8919	High Similarity	NPC174964
0.8919	High Similarity	NPC273366
0.8919	High Similarity	NPC195155
0.8919	High Similarity	NPC97534
0.8889	High Similarity	NPC477929
0.8875	High Similarity	NPC472272
0.8861	High Similarity	NPC473336
0.8861	High Similarity	NPC471044
0.8831	High Similarity	NPC477851
0.8816	High Similarity	NPC472608
0.88	High Similarity	NPC475742
0.88	High Similarity	NPC5767
0.88	High Similarity	NPC472486
0.88	High Similarity	NPC472487
0.8784	High Similarity	NPC254340
0.8784	High Similarity	NPC477930
0.8767	High Similarity	NPC469940
0.8767	High Similarity	NPC89310
0.875	High Similarity	NPC131892
0.875	High Similarity	NPC327728
0.875	High Similarity	NPC196197
0.875	High Similarity	NPC6120
0.875	High Similarity	NPC213178
0.8718	High Similarity	NPC469745
0.8684	High Similarity	NPC180199
0.8684	High Similarity	NPC221420
0.8684	High Similarity	NPC23884
0.8684	High Similarity	NPC477919
0.8667	High Similarity	NPC125767
0.8667	High Similarity	NPC472311
0.8667	High Similarity	NPC21220
0.8642	High Similarity	NPC302111
0.8642	High Similarity	NPC2783
0.863	High Similarity	NPC477850
0.8625	High Similarity	NPC319909
0.8592	High Similarity	NPC42060
0.8592	High Similarity	NPC268736
0.8592	High Similarity	NPC477931
0.8571	High Similarity	NPC476732
0.8571	High Similarity	NPC199965
0.8553	High Similarity	NPC477933
0.8553	High Similarity	NPC477932
0.8537	High Similarity	NPC33768
0.8537	High Similarity	NPC269360
0.8537	High Similarity	NPC264005
0.8537	High Similarity	NPC252714
0.8519	High Similarity	NPC294438
0.8519	High Similarity	NPC264317
0.85	High Similarity	NPC327451
0.8493	Intermediate Similarity	NPC64466
0.8452	Intermediate Similarity	NPC77756
0.8442	Intermediate Similarity	NPC477918
0.8434	Intermediate Similarity	NPC16377
0.8434	Intermediate Similarity	NPC474719
0.8421	Intermediate Similarity	NPC159789
0.8421	Intermediate Similarity	NPC477934
0.8415	Intermediate Similarity	NPC12774
0.84	Intermediate Similarity	NPC310766
0.8395	Intermediate Similarity	NPC50438
0.8395	Intermediate Similarity	NPC473299
0.8378	Intermediate Similarity	NPC108131
0.8375	Intermediate Similarity	NPC268040
0.8354	Intermediate Similarity	NPC470609
0.8353	Intermediate Similarity	NPC52756
0.8333	Intermediate Similarity	NPC31031
0.8333	Intermediate Similarity	NPC243594
0.8333	Intermediate Similarity	NPC56962
0.8333	Intermediate Similarity	NPC24705
0.8333	Intermediate Similarity	NPC213832
0.8333	Intermediate Similarity	NPC26029
0.8333	Intermediate Similarity	NPC220498
0.8333	Intermediate Similarity	NPC57954
0.8333	Intermediate Similarity	NPC471045
0.8312	Intermediate Similarity	NPC471046
0.8289	Intermediate Similarity	NPC133922
0.8272	Intermediate Similarity	NPC471037
0.8256	Intermediate Similarity	NPC291373
0.8256	Intermediate Similarity	NPC472232
0.8256	Intermediate Similarity	NPC472231
0.8256	Intermediate Similarity	NPC476189
0.825	Intermediate Similarity	NPC474870
0.825	Intermediate Similarity	NPC271572
0.825	Intermediate Similarity	NPC73515
0.825	Intermediate Similarity	NPC476071
0.825	Intermediate Similarity	NPC48756
0.825	Intermediate Similarity	NPC280781
0.8243	Intermediate Similarity	NPC321732
0.8243	Intermediate Similarity	NPC66407
0.8243	Intermediate Similarity	NPC474962
0.8243	Intermediate Similarity	NPC324607
0.8235	Intermediate Similarity	NPC169933
0.8228	Intermediate Similarity	NPC220379
0.8228	Intermediate Similarity	NPC472310
0.8228	Intermediate Similarity	NPC476176
0.8219	Intermediate Similarity	NPC41542
0.8219	Intermediate Similarity	NPC474221
0.8219	Intermediate Similarity	NPC130459
0.8219	Intermediate Similarity	NPC478180
0.8214	Intermediate Similarity	NPC4309
0.8214	Intermediate Similarity	NPC471900
0.8214	Intermediate Similarity	NPC146937
0.8205	Intermediate Similarity	NPC471151
0.8205	Intermediate Similarity	NPC212453
0.8205	Intermediate Similarity	NPC474404
0.8205	Intermediate Similarity	NPC264602
0.8205	Intermediate Similarity	NPC307865
0.8194	Intermediate Similarity	NPC230047
0.8194	Intermediate Similarity	NPC19311
0.8193	Intermediate Similarity	NPC476727
0.8193	Intermediate Similarity	NPC476726
0.8169	Intermediate Similarity	NPC114891
0.8161	Intermediate Similarity	NPC277399
0.8158	Intermediate Similarity	NPC477229
0.8158	Intermediate Similarity	NPC68426
0.8158	Intermediate Similarity	NPC282905
0.8148	Intermediate Similarity	NPC60018
0.8148	Intermediate Similarity	NPC328007
0.8148	Intermediate Similarity	NPC317066
0.8148	Intermediate Similarity	NPC154043
0.8148	Intermediate Similarity	NPC13494
0.8148	Intermediate Similarity	NPC477935
0.8148	Intermediate Similarity	NPC202688
0.814	Intermediate Similarity	NPC160506
0.8133	Intermediate Similarity	NPC232925
0.8133	Intermediate Similarity	NPC63588
0.8133	Intermediate Similarity	NPC251201
0.8125	Intermediate Similarity	NPC472853
0.8118	Intermediate Similarity	NPC271974
0.8118	Intermediate Similarity	NPC475921
0.8118	Intermediate Similarity	NPC247312
0.8118	Intermediate Similarity	NPC474704
0.8108	Intermediate Similarity	NPC472741
0.8095	Intermediate Similarity	NPC142361
0.8095	Intermediate Similarity	NPC263802
0.8095	Intermediate Similarity	NPC202937
0.8095	Intermediate Similarity	NPC239938
0.8095	Intermediate Similarity	NPC474684
0.8082	Intermediate Similarity	NPC44122
0.8082	Intermediate Similarity	NPC142712
0.8077	Intermediate Similarity	NPC108840
0.8072	Intermediate Similarity	NPC62572
0.8068	Intermediate Similarity	NPC287354
0.8068	Intermediate Similarity	NPC62407
0.8068	Intermediate Similarity	NPC205173
0.8052	Intermediate Similarity	NPC472854
0.8052	Intermediate Similarity	NPC168511
0.8052	Intermediate Similarity	NPC159325
0.8049	Intermediate Similarity	NPC475726
0.8049	Intermediate Similarity	NPC477285
0.8049	Intermediate Similarity	NPC245866
0.8049	Intermediate Similarity	NPC472743
0.8049	Intermediate Similarity	NPC111582
0.8049	Intermediate Similarity	NPC259173
0.8046	Intermediate Similarity	NPC473690
0.8046	Intermediate Similarity	NPC287118
0.8046	Intermediate Similarity	NPC470376
0.8046	Intermediate Similarity	NPC471902
0.8046	Intermediate Similarity	NPC470375
0.8046	Intermediate Similarity	NPC244356
0.8046	Intermediate Similarity	NPC224060
0.8028	Intermediate Similarity	NPC148174
0.8028	Intermediate Similarity	NPC71460
0.8028	Intermediate Similarity	NPC218585
0.8026	Intermediate Similarity	NPC157422
0.8026	Intermediate Similarity	NPC472309
0.8026	Intermediate Similarity	NPC470071

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 NPC317913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	3276
0.2-0.3	3653
0.3-0.4	1161
0.4-0.5	300
0.5-0.6	189
0.6-0.7	170
0.7-0.8	21
0.8-0.85	14
0.85-0.9	5
0.9-0.95	2
0.95-1	7

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6116	Phase 1
0.9859	High Similarity	NPD6117	Approved
0.9589	High Similarity	NPD6115	Approved
0.9589	High Similarity	NPD6118	Approved
0.9589	High Similarity	NPD6114	Approved
0.9589	High Similarity	NPD6697	Approved
0.9577	High Similarity	NPD6113	Clinical (unspecified phase)
0.9028	High Similarity	NPD4809	Clinical (unspecified phase)
0.9028	High Similarity	NPD4808	Clinical (unspecified phase)
0.875	High Similarity	NPD3700	Clinical (unspecified phase)
0.875	High Similarity	NPD3699	Clinical (unspecified phase)
0.8519	High Similarity	NPD7520	Clinical (unspecified phase)
0.8514	High Similarity	NPD6081	Approved
0.8421	Intermediate Similarity	NPD3703	Phase 2
0.8378	Intermediate Similarity	NPD4245	Approved
0.8378	Intermediate Similarity	NPD4244	Approved
0.8378	Intermediate Similarity	NPD4789	Approved
0.8356	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD5360	Phase 3
0.8333	Intermediate Similarity	NPD4224	Phase 2
0.8243	Intermediate Similarity	NPD3698	Phase 2
0.8194	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD8035	Phase 2
0.814	Intermediate Similarity	NPD8034	Phase 2
0.8026	Intermediate Similarity	NPD5777	Approved
0.8	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3702	Approved
0.7875	Intermediate Similarity	NPD3671	Phase 1
0.7792	Intermediate Similarity	NPD4758	Discontinued
0.7654	Intermediate Similarity	NPD5364	Discontinued
0.7527	Intermediate Similarity	NPD8418	Phase 2
0.7444	Intermediate Similarity	NPD6399	Phase 3
0.7436	Intermediate Similarity	NPD4787	Phase 1
0.7333	Intermediate Similarity	NPD7515	Phase 2
0.7326	Intermediate Similarity	NPD4786	Approved
0.7303	Intermediate Similarity	NPD5328	Approved
0.7262	Intermediate Similarity	NPD7525	Registered
0.726	Intermediate Similarity	NPD3198	Approved
0.7209	Intermediate Similarity	NPD4788	Approved
0.7159	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7093	Intermediate Similarity	NPD3667	Approved
0.7065	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD6928	Phase 2
0.7053	Intermediate Similarity	NPD7638	Approved
0.7042	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6881	Approved
0.7	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD7320	Approved
0.6989	Remote Similarity	NPD7748	Approved
0.6979	Remote Similarity	NPD7639	Approved
0.6979	Remote Similarity	NPD7640	Approved
0.6947	Remote Similarity	NPD4755	Approved
0.6947	Remote Similarity	NPD7902	Approved
0.6931	Remote Similarity	NPD6373	Approved
0.6931	Remote Similarity	NPD6372	Approved
0.69	Remote Similarity	NPD5701	Approved
0.69	Remote Similarity	NPD5697	Approved
0.6869	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6883	Approved
0.6863	Remote Similarity	NPD7102	Approved
0.6863	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD5221	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6837	Remote Similarity	NPD7632	Discontinued
0.6832	Remote Similarity	NPD6011	Approved
0.6804	Remote Similarity	NPD4700	Approved
0.6804	Remote Similarity	NPD4696	Approved
0.6804	Remote Similarity	NPD5285	Approved
0.6804	Remote Similarity	NPD5286	Approved
0.6796	Remote Similarity	NPD6869	Approved
0.6796	Remote Similarity	NPD6650	Approved
0.6796	Remote Similarity	NPD6617	Approved
0.6796	Remote Similarity	NPD8130	Phase 1
0.6796	Remote Similarity	NPD6847	Approved
0.6796	Remote Similarity	NPD6649	Approved
0.6796	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6083	Phase 2
0.6771	Remote Similarity	NPD6084	Phase 2
0.6771	Remote Similarity	NPD5173	Approved
0.6765	Remote Similarity	NPD6014	Approved
0.6765	Remote Similarity	NPD6012	Approved
0.6765	Remote Similarity	NPD6013	Approved
0.6742	Remote Similarity	NPD3665	Phase 1
0.6742	Remote Similarity	NPD3133	Approved
0.6742	Remote Similarity	NPD3666	Approved
0.6735	Remote Similarity	NPD5223	Approved
0.6731	Remote Similarity	NPD6882	Approved
0.6731	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD8298	Phase 2
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD4633	Approved
0.6632	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7900	Approved
0.663	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6672	Approved
0.663	Remote Similarity	NPD5737	Approved
0.66	Remote Similarity	NPD4754	Approved
0.66	Remote Similarity	NPD5174	Approved
0.66	Remote Similarity	NPD5175	Approved
0.6593	Remote Similarity	NPD7334	Approved
0.6593	Remote Similarity	NPD5330	Approved
0.6593	Remote Similarity	NPD7146	Approved
0.6593	Remote Similarity	NPD6684	Approved
0.6593	Remote Similarity	NPD6409	Approved
0.6593	Remote Similarity	NPD7521	Approved
0.6559	Remote Similarity	NPD4753	Phase 2
0.6556	Remote Similarity	NPD3668	Phase 3
0.6542	Remote Similarity	NPD6940	Discontinued
0.6535	Remote Similarity	NPD5141	Approved
0.6509	Remote Similarity	NPD4632	Approved
0.6509	Remote Similarity	NPD8133	Approved
0.6471	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD6920	Discontinued
0.6471	Remote Similarity	NPD7339	Approved
0.6471	Remote Similarity	NPD4768	Approved
0.6471	Remote Similarity	NPD6942	Approved
0.6456	Remote Similarity	NPD7909	Approved
0.6452	Remote Similarity	NPD6903	Approved
0.6437	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3617	Approved
0.6422	Remote Similarity	NPD6335	Approved
0.6421	Remote Similarity	NPD5284	Approved
0.6421	Remote Similarity	NPD5281	Approved
0.6413	Remote Similarity	NPD5279	Phase 3
0.6413	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1700	Approved
0.6392	Remote Similarity	NPD5695	Phase 3
0.6392	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6274	Approved
0.6389	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6364	Remote Similarity	NPD7100	Approved
0.6354	Remote Similarity	NPD8171	Discontinued
0.6351	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4729	Approved
0.6346	Remote Similarity	NPD4730	Approved
0.6346	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5128	Approved
0.6341	Remote Similarity	NPD6705	Phase 1
0.6333	Remote Similarity	NPD4221	Approved
0.6333	Remote Similarity	NPD4223	Phase 3
0.633	Remote Similarity	NPD6009	Approved
0.633	Remote Similarity	NPD7115	Discovery
0.633	Remote Similarity	NPD6317	Approved
0.6316	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6700	Approved
0.6311	Remote Similarity	NPD6008	Approved
0.6304	Remote Similarity	NPD5329	Approved
0.6286	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6313	Approved
0.6273	Remote Similarity	NPD6314	Approved
0.625	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD4802	Phase 2
0.625	Remote Similarity	NPD6703	Approved
0.625	Remote Similarity	NPD6702	Approved
0.625	Remote Similarity	NPD4238	Approved
0.6237	Remote Similarity	NPD6098	Approved
0.6226	Remote Similarity	NPD5249	Phase 3
0.6226	Remote Similarity	NPD5169	Approved
0.6226	Remote Similarity	NPD5135	Approved
0.6226	Remote Similarity	NPD5251	Approved
0.6226	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4634	Approved
0.6226	Remote Similarity	NPD5247	Approved
0.6226	Remote Similarity	NPD5248	Approved
0.6226	Remote Similarity	NPD5250	Approved
0.6224	Remote Similarity	NPD4629	Approved
0.6224	Remote Similarity	NPD5210	Approved
0.6222	Remote Similarity	NPD4692	Approved
0.6222	Remote Similarity	NPD4139	Approved
0.6211	Remote Similarity	NPD6673	Approved
0.6211	Remote Similarity	NPD6080	Approved
0.6211	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6904	Approved
0.6207	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4197	Approved
0.619	Remote Similarity	NPD5168	Approved
0.619	Remote Similarity	NPD6415	Discontinued
0.618	Remote Similarity	NPD7645	Phase 2
0.6174	Remote Similarity	NPD7507	Approved
0.6168	Remote Similarity	NPD5215	Approved
0.6168	Remote Similarity	NPD5217	Approved
0.6168	Remote Similarity	NPD5127	Approved
0.6168	Remote Similarity	NPD5216	Approved
0.6161	Remote Similarity	NPD6319	Approved
0.6145	Remote Similarity	NPD229	Approved
0.614	Remote Similarity	NPD7604	Phase 2

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