NPASS Compound

Structure

CID167702 OpenBabel06191715542D 27 30 0 0 1 0 0 0 0 0999 V2000 -2.8016 3.7046 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 -2.5298 2.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3401 3.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4604 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 -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 -4.7359 3.9073 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 -3.3730 2.9177 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9734 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6852 -0.9729 0.0000 C 0 0 1 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 -4.1646 4.6942 0.0000 C 0 0 0 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 -2.5295 1.4588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5513 -1.4727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1974 4.5928 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5603 5.5825 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 9 1 0 0 0 0 4 15 1 0 0 0 0 5 6 1 0 0 0 0 5 16 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 22 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 1 1 1 0 0 0 15 19 1 0 0 0 0 16 23 1 1 0 0 0 17 25 1 6 0 0 0 18 6 1 1 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 24 1 6 0 0 0 20 24 1 6 0 0 0 21 23 1 6 0 0 0 22 26 2 0 0 0 0 22 27 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:	376.3
Volume:	413.168
LogP:	5.663
LogD:	5.264
LogS:	-4.676
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	4.116
Fsp3:	0.958
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.928
MDCK Permeability:	3.601945718401112e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.354
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.746
30% Bioavailability (F30%):	0.585

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.067
Plasma Protein Binding (PPB):	95.96236419677734%
Volume Distribution (VD):	0.746
Pgp-substrate:	1.9094964265823364%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.435
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.852
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.377
CYP3A4-inhibitor:	0.068
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	6.981
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.41
Drug-inuced Liver Injury (DILI):	0.077
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.184
Skin Sensitization:	0.965
Carcinogencity:	0.093
Eye Corrosion:	0.801
Eye Irritation:	0.774
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC167702

Natural Product ID:	NPC167702
*Common Name:**	Isolithocholic Acid
IUPAC Name:	(4R)-4-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-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:	Isolithocholic Acid
Standard InCHIKey:	SMEROWZSTRWXGI-WFVDQZAMSA-N
Standard InCHI:	InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17+,18+,19-,20+,21+,23+,24-/m1/s1
SMILES:	C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL270067
PubChem CID:	164853
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:0000260] Monohydroxy 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
IC50	2
Ki	1

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1270	Individual Protein	Aldo-keto reductase family 1 member B10	Homo sapiens	Ki	=	15.0	nM	PMID[495022]
NPT1270	Individual Protein	Aldo-keto reductase family 1 member B10	Homo sapiens	IC50	=	27.0	nM	PMID[495023]
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	=	6900.0	nM	PMID[495023]

☑ 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 NPC167702 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	300
0.1-0.2	2920
0.2-0.3	13955
0.3-0.4	10174
0.4-0.5	5803
0.5-0.6	5102
0.6-0.7	3190
0.7-0.8	1036
0.8-0.85	117
0.85-0.9	56
0.9-0.95	38
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280026
0.9855	High Similarity	NPC212733
0.9714	High Similarity	NPC4209
0.9577	High Similarity	NPC143133
0.9577	High Similarity	NPC207010
0.9577	High Similarity	NPC298168
0.9577	High Similarity	NPC317913
0.9444	High Similarity	NPC80089
0.9444	High Similarity	NPC324700
0.9444	High Similarity	NPC185465
0.9444	High Similarity	NPC171426
0.9444	High Similarity	NPC34046
0.9444	High Similarity	NPC224802
0.942	High Similarity	NPC58057
0.942	High Similarity	NPC151018
0.942	High Similarity	NPC320549
0.942	High Similarity	NPC156277
0.9412	High Similarity	NPC319671
0.9412	High Similarity	NPC469941
0.9412	High Similarity	NPC252032
0.9412	High Similarity	NPC476734
0.9315	High Similarity	NPC201276
0.9315	High Similarity	NPC320144
0.9315	High Similarity	NPC80891
0.9286	High Similarity	NPC232112
0.9275	High Similarity	NPC477929
0.9178	High Similarity	NPC329117
0.9155	High Similarity	NPC254340
0.913	High Similarity	NPC213178
0.913	High Similarity	NPC6120
0.913	High Similarity	NPC131892
0.913	High Similarity	NPC327728
0.9067	High Similarity	NPC58631
0.9067	High Similarity	NPC12933
0.9028	High Similarity	NPC195155
0.9028	High Similarity	NPC273366
0.9028	High Similarity	NPC97534
0.9028	High Similarity	NPC174964
0.9	High Similarity	NPC477850
0.8971	High Similarity	NPC42060
0.8947	High Similarity	NPC61107
0.8947	High Similarity	NPC30583
0.8947	High Similarity	NPC121121
0.8947	High Similarity	NPC289486
0.8933	High Similarity	NPC477851
0.8933	High Similarity	NPC261616
0.8904	High Similarity	NPC475742
0.8904	High Similarity	NPC472486
0.8904	High Similarity	NPC5767
0.8904	High Similarity	NPC472487
0.8889	High Similarity	NPC477930
0.8873	High Similarity	NPC89310
0.8873	High Similarity	NPC469940
0.8857	High Similarity	NPC196197
0.8857	High Similarity	NPC64466
0.8784	High Similarity	NPC221420
0.8784	High Similarity	NPC180199
0.8784	High Similarity	NPC23884
0.8784	High Similarity	NPC475031
0.8784	High Similarity	NPC477919
0.8767	High Similarity	NPC21220
0.8767	High Similarity	NPC472311
0.8767	High Similarity	NPC125767
0.875	High Similarity	NPC310766
0.8732	High Similarity	NPC108131
0.8718	High Similarity	NPC471044
0.8718	High Similarity	NPC473336
0.8696	High Similarity	NPC268736
0.8696	High Similarity	NPC477931
0.8667	High Similarity	NPC476732
0.8667	High Similarity	NPC199965
0.8649	High Similarity	NPC477932
0.8649	High Similarity	NPC477933
0.863	High Similarity	NPC133922
0.8608	High Similarity	NPC294438
0.8608	High Similarity	NPC264317
0.8592	High Similarity	NPC324607
0.8592	High Similarity	NPC321732
0.8592	High Similarity	NPC474962
0.8571	High Similarity	NPC130459
0.8571	High Similarity	NPC474221
0.8571	High Similarity	NPC478180
0.8533	High Similarity	NPC477918
0.8533	High Similarity	NPC474404
0.8529	High Similarity	NPC114891
0.8514	High Similarity	NPC477934
0.8514	High Similarity	NPC159789
0.85	High Similarity	NPC472272
0.85	High Similarity	NPC302111
0.85	High Similarity	NPC12774
0.85	High Similarity	NPC2783
0.8481	Intermediate Similarity	NPC319909
0.8442	Intermediate Similarity	NPC470609
0.8421	Intermediate Similarity	NPC472608
0.8421	Intermediate Similarity	NPC26029
0.8395	Intermediate Similarity	NPC33768
0.8395	Intermediate Similarity	NPC252714
0.8395	Intermediate Similarity	NPC264005
0.8395	Intermediate Similarity	NPC269360
0.8382	Intermediate Similarity	NPC148174
0.8382	Intermediate Similarity	NPC218585
0.8382	Intermediate Similarity	NPC71460
0.8378	Intermediate Similarity	NPC472854
0.8356	Intermediate Similarity	NPC473267
0.8354	Intermediate Similarity	NPC245866
0.8333	Intermediate Similarity	NPC48756
0.8333	Intermediate Similarity	NPC280781
0.8333	Intermediate Similarity	NPC469745
0.8312	Intermediate Similarity	NPC472310
0.831	Intermediate Similarity	NPC41542
0.8293	Intermediate Similarity	NPC471900
0.8293	Intermediate Similarity	NPC474719
0.8293	Intermediate Similarity	NPC146937
0.8293	Intermediate Similarity	NPC16377
0.8289	Intermediate Similarity	NPC264602
0.8286	Intermediate Similarity	NPC230047
0.8286	Intermediate Similarity	NPC19311
0.8267	Intermediate Similarity	NPC27349
0.8267	Intermediate Similarity	NPC24014
0.8243	Intermediate Similarity	NPC477229
0.8243	Intermediate Similarity	NPC282905
0.8243	Intermediate Similarity	NPC68426
0.8228	Intermediate Similarity	NPC317066
0.8228	Intermediate Similarity	NPC328007
0.8228	Intermediate Similarity	NPC268040
0.8228	Intermediate Similarity	NPC477935
0.8219	Intermediate Similarity	NPC476731
0.8205	Intermediate Similarity	NPC472853
0.8194	Intermediate Similarity	NPC473225
0.8193	Intermediate Similarity	NPC57954
0.8193	Intermediate Similarity	NPC24705
0.8193	Intermediate Similarity	NPC213832
0.8193	Intermediate Similarity	NPC220498
0.8193	Intermediate Similarity	NPC56962
0.8182	Intermediate Similarity	NPC243594
0.8182	Intermediate Similarity	NPC31031
0.8171	Intermediate Similarity	NPC474684
0.8171	Intermediate Similarity	NPC142361
0.8169	Intermediate Similarity	NPC142712
0.8158	Intermediate Similarity	NPC471046
0.8143	Intermediate Similarity	NPC167995
0.8143	Intermediate Similarity	NPC281540
0.8143	Intermediate Similarity	NPC69149
0.8143	Intermediate Similarity	NPC159654
0.8143	Intermediate Similarity	NPC118937
0.8133	Intermediate Similarity	NPC168511
0.8133	Intermediate Similarity	NPC130011
0.8133	Intermediate Similarity	NPC159325
0.8125	Intermediate Similarity	NPC259173
0.8125	Intermediate Similarity	NPC471037
0.8125	Intermediate Similarity	NPC475726
0.8125	Intermediate Similarity	NPC327451
0.8125	Intermediate Similarity	NPC472743
0.8108	Intermediate Similarity	NPC126642
0.8108	Intermediate Similarity	NPC472309
0.8101	Intermediate Similarity	NPC476071
0.8095	Intermediate Similarity	NPC77756
0.8095	Intermediate Similarity	NPC169933
0.8077	Intermediate Similarity	NPC220379
0.8072	Intermediate Similarity	NPC4309
0.8056	Intermediate Similarity	NPC475884
0.8056	Intermediate Similarity	NPC48079
0.8056	Intermediate Similarity	NPC473230
0.8056	Intermediate Similarity	NPC472984
0.8052	Intermediate Similarity	NPC212453
0.8052	Intermediate Similarity	NPC66105
0.8052	Intermediate Similarity	NPC471151
0.8049	Intermediate Similarity	NPC55309
0.8049	Intermediate Similarity	NPC92139
0.8049	Intermediate Similarity	NPC80590
0.8049	Intermediate Similarity	NPC155011
0.8049	Intermediate Similarity	NPC70661
0.8049	Intermediate Similarity	NPC28252
0.8028	Intermediate Similarity	NPC473276
0.8028	Intermediate Similarity	NPC474380
0.8028	Intermediate Similarity	NPC41577
0.8026	Intermediate Similarity	NPC179858
0.8026	Intermediate Similarity	NPC267753
0.8025	Intermediate Similarity	NPC264665
0.8025	Intermediate Similarity	NPC474996
0.8025	Intermediate Similarity	NPC474233
0.8025	Intermediate Similarity	NPC74595
0.8025	Intermediate Similarity	NPC475745
0.8025	Intermediate Similarity	NPC263974
0.8025	Intermediate Similarity	NPC50438
0.8025	Intermediate Similarity	NPC474482
0.8025	Intermediate Similarity	NPC473299
0.8	Intermediate Similarity	NPC311642
0.8	Intermediate Similarity	NPC52756
0.8	Intermediate Similarity	NPC164289
0.8	Intermediate Similarity	NPC477936
0.8	Intermediate Similarity	NPC475416
0.8	Intermediate Similarity	NPC242771
0.8	Intermediate Similarity	NPC13494
0.8	Intermediate Similarity	NPC100366
0.8	Intermediate Similarity	NPC81759
0.8	Intermediate Similarity	NPC170985
0.7976	Intermediate Similarity	NPC247312
0.7976	Intermediate Similarity	NPC474704
0.7976	Intermediate Similarity	NPC475921

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 NPC167702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	3306
0.2-0.3	3705
0.3-0.4	1098
0.4-0.5	269
0.5-0.6	226
0.6-0.7	158
0.7-0.8	16
0.8-0.85	5
0.85-0.9	10
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD6113	Clinical (unspecified phase)
0.9714	High Similarity	NPD6117	Approved
0.9577	High Similarity	NPD6116	Phase 1
0.9444	High Similarity	NPD6114	Approved
0.9444	High Similarity	NPD6697	Approved
0.9444	High Similarity	NPD6115	Approved
0.9444	High Similarity	NPD6118	Approved
0.942	High Similarity	NPD4808	Clinical (unspecified phase)
0.942	High Similarity	NPD4809	Clinical (unspecified phase)
0.913	High Similarity	NPD3699	Clinical (unspecified phase)
0.913	High Similarity	NPD3700	Clinical (unspecified phase)
0.8732	High Similarity	NPD4245	Approved
0.8732	High Similarity	NPD4244	Approved
0.8732	High Similarity	NPD4789	Approved
0.8714	High Similarity	NPD5360	Phase 3
0.8714	High Similarity	NPD5361	Clinical (unspecified phase)
0.8696	High Similarity	NPD4224	Phase 2
0.8611	High Similarity	NPD6081	Approved
0.8608	High Similarity	NPD7520	Clinical (unspecified phase)
0.8592	High Similarity	NPD3698	Phase 2
0.8551	High Similarity	NPD3171	Clinical (unspecified phase)
0.8514	High Similarity	NPD3703	Phase 2
0.8356	Intermediate Similarity	NPD5777	Approved
0.8267	Intermediate Similarity	NPD3702	Approved
0.8182	Intermediate Similarity	NPD3671	Phase 1
0.8108	Intermediate Similarity	NPD4758	Discontinued
0.7838	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD8034	Phase 2
0.7791	Intermediate Similarity	NPD8035	Phase 2
0.7733	Intermediate Similarity	NPD4787	Phase 1
0.7722	Intermediate Similarity	NPD5364	Discontinued
0.759	Intermediate Similarity	NPD4786	Approved
0.7571	Intermediate Similarity	NPD3198	Approved
0.747	Intermediate Similarity	NPD4788	Approved
0.7391	Intermediate Similarity	NPD8418	Phase 2
0.7356	Intermediate Similarity	NPD5328	Approved
0.7349	Intermediate Similarity	NPD3667	Approved
0.7303	Intermediate Similarity	NPD6399	Phase 3
0.7209	Intermediate Similarity	NPD3618	Phase 1
0.7191	Intermediate Similarity	NPD7515	Phase 2
0.7191	Intermediate Similarity	NPD6079	Approved
0.7108	Intermediate Similarity	NPD6928	Phase 2
0.7101	Intermediate Similarity	NPD3729	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3665	Phase 1
0.6977	Remote Similarity	NPD3133	Approved
0.6977	Remote Similarity	NPD3666	Approved
0.6923	Remote Similarity	NPD4202	Approved
0.6915	Remote Similarity	NPD7638	Approved
0.6905	Remote Similarity	NPD7525	Registered
0.6854	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7748	Approved
0.6842	Remote Similarity	NPD7640	Approved
0.6842	Remote Similarity	NPD7639	Approved
0.6837	Remote Similarity	NPD6675	Approved
0.6837	Remote Similarity	NPD7128	Approved
0.6837	Remote Similarity	NPD5739	Approved
0.6837	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6684	Approved
0.6818	Remote Similarity	NPD7521	Approved
0.6818	Remote Similarity	NPD6409	Approved
0.6818	Remote Similarity	NPD7334	Approved
0.6818	Remote Similarity	NPD5330	Approved
0.6818	Remote Similarity	NPD7146	Approved
0.6809	Remote Similarity	NPD6083	Phase 2
0.6809	Remote Similarity	NPD6084	Phase 2
0.6735	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7339	Approved
0.6707	Remote Similarity	NPD6942	Approved
0.6702	Remote Similarity	NPD4697	Phase 3
0.6702	Remote Similarity	NPD5222	Approved
0.6702	Remote Similarity	NPD5221	Approved
0.6702	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7632	Discontinued
0.67	Remote Similarity	NPD6881	Approved
0.67	Remote Similarity	NPD6899	Approved
0.67	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6634	Remote Similarity	NPD6372	Approved
0.6634	Remote Similarity	NPD6373	Approved
0.6632	Remote Similarity	NPD7902	Approved
0.6632	Remote Similarity	NPD4755	Approved
0.6632	Remote Similarity	NPD5173	Approved
0.6629	Remote Similarity	NPD5279	Phase 3
0.662	Remote Similarity	NPD615	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5701	Approved
0.66	Remote Similarity	NPD5697	Approved
0.6593	Remote Similarity	NPD4753	Phase 2
0.6591	Remote Similarity	NPD3668	Phase 3
0.6582	Remote Similarity	NPD6705	Phase 1
0.6569	Remote Similarity	NPD7290	Approved
0.6569	Remote Similarity	NPD7102	Approved
0.6569	Remote Similarity	NPD6883	Approved
0.6552	Remote Similarity	NPD4221	Approved
0.6552	Remote Similarity	NPD4223	Phase 3
0.6538	Remote Similarity	NPD8298	Phase 2
0.6535	Remote Similarity	NPD6011	Approved
0.6517	Remote Similarity	NPD5329	Approved
0.6505	Remote Similarity	NPD6649	Approved
0.6505	Remote Similarity	NPD6869	Approved
0.6505	Remote Similarity	NPD6847	Approved
0.6505	Remote Similarity	NPD6617	Approved
0.6505	Remote Similarity	NPD6650	Approved
0.6505	Remote Similarity	NPD8130	Phase 1
0.6505	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6920	Discontinued
0.6495	Remote Similarity	NPD4696	Approved
0.6495	Remote Similarity	NPD5285	Approved
0.6495	Remote Similarity	NPD4700	Approved
0.6495	Remote Similarity	NPD5286	Approved
0.6494	Remote Similarity	NPD7909	Approved
0.6471	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD6014	Approved
0.6471	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6012	Approved
0.6444	Remote Similarity	NPD6098	Approved
0.6442	Remote Similarity	NPD6882	Approved
0.6442	Remote Similarity	NPD8297	Approved
0.6437	Remote Similarity	NPD4692	Approved
0.6437	Remote Similarity	NPD4139	Approved
0.6429	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5223	Approved
0.6421	Remote Similarity	NPD5695	Phase 3
0.6415	Remote Similarity	NPD6940	Discontinued
0.6404	Remote Similarity	NPD4197	Approved
0.6392	Remote Similarity	NPD5696	Approved
0.6381	Remote Similarity	NPD8133	Approved
0.6373	Remote Similarity	NPD6415	Discontinued
0.6364	Remote Similarity	NPD4633	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD5224	Approved
0.6364	Remote Similarity	NPD5226	Approved
0.6364	Remote Similarity	NPD5225	Approved
0.6322	Remote Similarity	NPD4748	Discontinued
0.6316	Remote Similarity	NPD7900	Approved
0.6316	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5174	Approved
0.63	Remote Similarity	NPD4754	Approved
0.63	Remote Similarity	NPD5175	Approved
0.6279	Remote Similarity	NPD4802	Phase 2
0.6279	Remote Similarity	NPD4238	Approved
0.6277	Remote Similarity	NPD5281	Approved
0.6277	Remote Similarity	NPD5284	Approved
0.6264	Remote Similarity	NPD4138	Approved
0.6264	Remote Similarity	NPD4690	Approved
0.6264	Remote Similarity	NPD4688	Approved
0.6264	Remote Similarity	NPD4689	Approved
0.6264	Remote Similarity	NPD4693	Phase 3
0.6264	Remote Similarity	NPD5205	Approved
0.6264	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6868	Approved
0.625	Remote Similarity	NPD5210	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4629	Approved
0.6238	Remote Similarity	NPD5141	Approved
0.6237	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6904	Approved
0.6237	Remote Similarity	NPD6673	Approved
0.6237	Remote Similarity	NPD6080	Approved
0.6226	Remote Similarity	NPD4632	Approved
0.6211	Remote Similarity	NPD8171	Discontinued
0.6207	Remote Similarity	NPD7645	Phase 2
0.6204	Remote Similarity	NPD7115	Discovery
0.619	Remote Similarity	NPD6924	Approved
0.619	Remote Similarity	NPD6926	Approved
0.6176	Remote Similarity	NPD4767	Approved
0.6176	Remote Similarity	NPD4768	Approved
0.6176	Remote Similarity	NPD634	Phase 3
0.617	Remote Similarity	NPD6700	Approved
0.617	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6335	Approved
0.6129	Remote Similarity	NPD5208	Approved
0.6125	Remote Similarity	NPD375	Phase 2
0.6111	Remote Similarity	NPD3186	Phase 1
0.6111	Remote Similarity	NPD6274	Approved
0.6105	Remote Similarity	NPD6703	Approved
0.6105	Remote Similarity	NPD6702	Approved
0.6105	Remote Similarity	NPD6411	Approved
0.61	Remote Similarity	NPD1700	Approved
0.6098	Remote Similarity	NPD3725	Approved
0.6098	Remote Similarity	NPD3726	Approved
0.6091	Remote Similarity	NPD7101	Approved
0.6091	Remote Similarity	NPD7100	Approved
0.6087	Remote Similarity	NPD5280	Approved
0.6087	Remote Similarity	NPD384	Approved
0.6087	Remote Similarity	NPD385	Approved
0.6087	Remote Similarity	NPD4694	Approved
0.6087	Remote Similarity	NPD5690	Phase 2
0.6058	Remote Similarity	NPD5168	Approved
0.6058	Remote Similarity	NPD4730	Approved
0.6058	Remote Similarity	NPD4729	Approved
0.6058	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5128	Approved
0.6055	Remote Similarity	NPD6317	Approved
0.6055	Remote Similarity	NPD6009	Approved
0.6047	Remote Similarity	NPD6933	Approved
0.6019	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)

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