NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	402.31
Volume:	439.204
LogP:	5.204
LogD:	4.1
LogS:	-5.037
# Rotatable Bonds:	1
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	4.976
Fsp3:	0.923
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.746
MDCK Permeability:	1.7719627066981047e-05
Pgp-inhibitor:	0.93
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.815
30% Bioavailability (F30%):	0.376

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.352
Plasma Protein Binding (PPB):	96.07611846923828%
Volume Distribution (VD):	1.944
Pgp-substrate:	3.1977899074554443%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.438
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.15
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.357
CYP3A4-inhibitor:	0.211
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	10.023
Half-life (T1/2):	0.023

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.126
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.783
Skin Sensitization:	0.095
Carcinogencity:	0.054
Eye Corrosion:	0.301
Eye Irritation:	0.295
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC477970

Natural Product ID:	NPC477970
*Common Name:**	(1R,5bR,11aS,13R,13aS,13bS)-1-methoxy-5b,8,8,11a,13a-pentamethyl-1,3,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a,13b-octadecahydrochryseno[2,1-c]furan-13-ol
IUPAC Name:	(1R,5bR,11aS,13R,13aS,13bS)-1-methoxy-5b,8,8,11a,13a-pentamethyl-1,3,5,5a,6,7,7a,9,10,11,11b,12,13,13b-tetradecahydrophenanthro[2,1-e][2]benzofuran-13-ol
Synonyms:
Standard InCHIKey:	BIJAKZXAJWXIHK-QWABTNDYSA-N
Standard InCHI:	InChI=1S/C26H42O3/c1-23(2)11-7-12-24(3)17(23)10-13-25(4)18-9-8-16-15-29-22(28-6)21(16)26(18,5)20(27)14-19(24)25/h8,17-22,27H,7,9-15H2,1-6H3/t17?,18?,19?,20-,21-,22-,24+,25+,26-/m1/s1
SMILES:	C[C@]12CCCC(C1CC[C@@]3(C2C[C@H]([C@]4(C3CC=C5[C@@H]4[C@@H](OC5)OC)C)O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	21778740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tongoa, Vanuatu Islands	1996	PMID[10757711]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662110]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497946]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Tong-Yong City in the South Sea, Korea	n.a.	PMID[16905319]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17567172]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988093]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18407692]
NPO33376	Spongia sp.	Species	Spongiidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[24992702]

☑ 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	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	IC50	=	24800	nM	PMID[16905319]
NPT27	Others	Unspecified		IC50	=	86900	nM	PMID[16905319]

☑ 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 NPC477970 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	199
0.1-0.2	1596
0.2-0.3	4919
0.3-0.4	12192
0.4-0.5	10352
0.5-0.6	6038
0.6-0.7	4873
0.7-0.8	2262
0.8-0.85	224
0.85-0.9	24
0.9-0.95	13
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100892
0.9886	High Similarity	NPC189513
0.9775	High Similarity	NPC477969
0.9775	High Similarity	NPC135224
0.9355	High Similarity	NPC477968
0.9355	High Similarity	NPC477971
0.9355	High Similarity	NPC161527
0.9355	High Similarity	NPC20113
0.9355	High Similarity	NPC228251
0.9355	High Similarity	NPC477972
0.9355	High Similarity	NPC219285
0.9213	High Similarity	NPC470819
0.9111	High Similarity	NPC470817
0.9091	High Similarity	NPC173917
0.9032	High Similarity	NPC94905
0.9032	High Similarity	NPC8954
0.8969	High Similarity	NPC222161
0.8764	High Similarity	NPC119001
0.8673	High Similarity	NPC471888
0.8673	High Similarity	NPC471885
0.8673	High Similarity	NPC473124
0.8673	High Similarity	NPC471886
0.8673	High Similarity	NPC473123
0.8673	High Similarity	NPC471450
0.8673	High Similarity	NPC471887
0.8587	High Similarity	NPC477917
0.8586	High Similarity	NPC110656
0.8586	High Similarity	NPC203354
0.8586	High Similarity	NPC93352
0.8586	High Similarity	NPC473127
0.8571	High Similarity	NPC300399
0.8571	High Similarity	NPC238397
0.8571	High Similarity	NPC37207
0.8571	High Similarity	NPC471482
0.8571	High Similarity	NPC471363
0.8571	High Similarity	NPC471889
0.8515	High Similarity	NPC80210
0.8515	High Similarity	NPC38376
0.8485	Intermediate Similarity	NPC134270
0.8485	Intermediate Similarity	NPC127933
0.8485	Intermediate Similarity	NPC475889
0.8485	Intermediate Similarity	NPC7644
0.8485	Intermediate Similarity	NPC7613
0.8469	Intermediate Similarity	NPC176406
0.8462	Intermediate Similarity	NPC157441
0.8444	Intermediate Similarity	NPC46320
0.8431	Intermediate Similarity	NPC195116
0.8431	Intermediate Similarity	NPC472901
0.8431	Intermediate Similarity	NPC285253
0.8431	Intermediate Similarity	NPC250089
0.8431	Intermediate Similarity	NPC14630
0.8431	Intermediate Similarity	NPC157530
0.8431	Intermediate Similarity	NPC221110
0.8431	Intermediate Similarity	NPC180459
0.8427	Intermediate Similarity	NPC109938
0.8427	Intermediate Similarity	NPC122945
0.8421	Intermediate Similarity	NPC72817
0.8421	Intermediate Similarity	NPC477927
0.8421	Intermediate Similarity	NPC305160
0.8416	Intermediate Similarity	NPC281939
0.8416	Intermediate Similarity	NPC33053
0.84	Intermediate Similarity	NPC473207
0.84	Intermediate Similarity	NPC470321
0.84	Intermediate Similarity	NPC75608
0.84	Intermediate Similarity	NPC264867
0.84	Intermediate Similarity	NPC201880
0.84	Intermediate Similarity	NPC81567
0.8367	Intermediate Similarity	NPC146188
0.8367	Intermediate Similarity	NPC473790
0.8367	Intermediate Similarity	NPC64348
0.8365	Intermediate Similarity	NPC12046
0.8365	Intermediate Similarity	NPC194951
0.8351	Intermediate Similarity	NPC26307
0.8351	Intermediate Similarity	NPC97867
0.8351	Intermediate Similarity	NPC98112
0.8351	Intermediate Similarity	NPC240372
0.835	Intermediate Similarity	NPC191439
0.835	Intermediate Similarity	NPC103627
0.835	Intermediate Similarity	NPC170974
0.8333	Intermediate Similarity	NPC472189
0.8333	Intermediate Similarity	NPC471372
0.8333	Intermediate Similarity	NPC471362
0.8317	Intermediate Similarity	NPC172867
0.8317	Intermediate Similarity	NPC472900
0.8317	Intermediate Similarity	NPC472899
0.8317	Intermediate Similarity	NPC252296
0.8317	Intermediate Similarity	NPC472898
0.8316	Intermediate Similarity	NPC242419
0.8316	Intermediate Similarity	NPC235126
0.83	Intermediate Similarity	NPC473198
0.83	Intermediate Similarity	NPC162354
0.83	Intermediate Similarity	NPC120009
0.8298	Intermediate Similarity	NPC159876
0.8295	Intermediate Similarity	NPC17550
0.8283	Intermediate Similarity	NPC470434
0.8283	Intermediate Similarity	NPC21568
0.8283	Intermediate Similarity	NPC285231
0.8269	Intermediate Similarity	NPC65034
0.8269	Intermediate Similarity	NPC473021
0.8269	Intermediate Similarity	NPC472987
0.8269	Intermediate Similarity	NPC110494
0.8269	Intermediate Similarity	NPC157474
0.8269	Intermediate Similarity	NPC208189
0.8265	Intermediate Similarity	NPC234287
0.8265	Intermediate Similarity	NPC280825
0.8265	Intermediate Similarity	NPC216260
0.8265	Intermediate Similarity	NPC5358
0.8261	Intermediate Similarity	NPC323209
0.8252	Intermediate Similarity	NPC28844
0.8252	Intermediate Similarity	NPC473318
0.8252	Intermediate Similarity	NPC473328
0.8247	Intermediate Similarity	NPC90583
0.8247	Intermediate Similarity	NPC171598
0.8242	Intermediate Similarity	NPC319238
0.8235	Intermediate Similarity	NPC125423
0.8235	Intermediate Similarity	NPC109376
0.8235	Intermediate Similarity	NPC184512
0.8235	Intermediate Similarity	NPC88013
0.8222	Intermediate Similarity	NPC304285
0.8202	Intermediate Similarity	NPC206062
0.82	Intermediate Similarity	NPC136816
0.8191	Intermediate Similarity	NPC293044
0.8191	Intermediate Similarity	NPC473058
0.819	Intermediate Similarity	NPC231797
0.819	Intermediate Similarity	NPC473125
0.819	Intermediate Similarity	NPC476305
0.8182	Intermediate Similarity	NPC473200
0.8182	Intermediate Similarity	NPC282669
0.8182	Intermediate Similarity	NPC324841
0.8182	Intermediate Similarity	NPC469942
0.8182	Intermediate Similarity	NPC324598
0.8182	Intermediate Similarity	NPC477716
0.8182	Intermediate Similarity	NPC7341
0.8182	Intermediate Similarity	NPC477721
0.8173	Intermediate Similarity	NPC65155
0.8163	Intermediate Similarity	NPC476893
0.8163	Intermediate Similarity	NPC177818
0.8163	Intermediate Similarity	NPC76266
0.8163	Intermediate Similarity	NPC243728
0.8163	Intermediate Similarity	NPC472188
0.8163	Intermediate Similarity	NPC473890
0.8155	Intermediate Similarity	NPC217921
0.8155	Intermediate Similarity	NPC311223
0.8155	Intermediate Similarity	NPC135015
0.8155	Intermediate Similarity	NPC224660
0.8155	Intermediate Similarity	NPC48548
0.8155	Intermediate Similarity	NPC470024
0.8155	Intermediate Similarity	NPC128795
0.8144	Intermediate Similarity	NPC476894
0.8137	Intermediate Similarity	NPC218158
0.8137	Intermediate Similarity	NPC470055
0.8137	Intermediate Similarity	NPC470056
0.8125	Intermediate Similarity	NPC91654
0.8125	Intermediate Similarity	NPC67398
0.8125	Intermediate Similarity	NPC474792
0.8119	Intermediate Similarity	NPC45897
0.8119	Intermediate Similarity	NPC213190
0.8119	Intermediate Similarity	NPC99627
0.8119	Intermediate Similarity	NPC473129
0.8119	Intermediate Similarity	NPC281378
0.8113	Intermediate Similarity	NPC290608
0.8113	Intermediate Similarity	NPC40133
0.8113	Intermediate Similarity	NPC44298
0.8113	Intermediate Similarity	NPC49413
0.8113	Intermediate Similarity	NPC473128
0.8111	Intermediate Similarity	NPC476646
0.8105	Intermediate Similarity	NPC295668
0.8105	Intermediate Similarity	NPC92885
0.8105	Intermediate Similarity	NPC471432
0.8105	Intermediate Similarity	NPC77796
0.8105	Intermediate Similarity	NPC476226
0.8105	Intermediate Similarity	NPC471433
0.81	Intermediate Similarity	NPC129372
0.81	Intermediate Similarity	NPC160734
0.81	Intermediate Similarity	NPC472023
0.81	Intermediate Similarity	NPC263756
0.81	Intermediate Similarity	NPC474022
0.81	Intermediate Similarity	NPC88000
0.81	Intermediate Similarity	NPC309425
0.81	Intermediate Similarity	NPC4831
0.81	Intermediate Similarity	NPC47566
0.81	Intermediate Similarity	NPC117714
0.81	Intermediate Similarity	NPC477717
0.8095	Intermediate Similarity	NPC13190
0.8081	Intermediate Similarity	NPC471366
0.8081	Intermediate Similarity	NPC472186
0.8081	Intermediate Similarity	NPC477928
0.8081	Intermediate Similarity	NPC158088
0.8081	Intermediate Similarity	NPC476800
0.8081	Intermediate Similarity	NPC473154
0.8081	Intermediate Similarity	NPC476895
0.8081	Intermediate Similarity	NPC318917
0.8077	Intermediate Similarity	NPC316974
0.8077	Intermediate Similarity	NPC40728
0.8077	Intermediate Similarity	NPC112457
0.8077	Intermediate Similarity	NPC206618
0.8077	Intermediate Similarity	NPC128133
0.8073	Intermediate Similarity	NPC470914
0.8065	Intermediate Similarity	NPC118266
0.8061	Intermediate Similarity	NPC73858

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 NPC477970 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1725
0.2-0.3	3958
0.3-0.4	2223
0.4-0.5	619
0.5-0.6	241
0.6-0.7	170
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7723	Intermediate Similarity	NPD7638	Approved
0.7692	Intermediate Similarity	NPD7645	Phase 2
0.7658	Intermediate Similarity	NPD7327	Approved
0.7658	Intermediate Similarity	NPD7328	Approved
0.7647	Intermediate Similarity	NPD7640	Approved
0.7647	Intermediate Similarity	NPD7639	Approved
0.7611	Intermediate Similarity	NPD8033	Approved
0.7589	Intermediate Similarity	NPD7516	Approved
0.7522	Intermediate Similarity	NPD8377	Approved
0.7522	Intermediate Similarity	NPD8294	Approved
0.7456	Intermediate Similarity	NPD8378	Approved
0.7456	Intermediate Similarity	NPD8296	Approved
0.7456	Intermediate Similarity	NPD8380	Approved
0.7456	Intermediate Similarity	NPD8335	Approved
0.7456	Intermediate Similarity	NPD8379	Approved
0.7419	Intermediate Similarity	NPD7525	Registered
0.7315	Intermediate Similarity	NPD6686	Approved
0.7304	Intermediate Similarity	NPD7503	Approved
0.7253	Intermediate Similarity	NPD6942	Approved
0.7253	Intermediate Similarity	NPD7339	Approved
0.7222	Intermediate Similarity	NPD6412	Phase 2
0.7203	Intermediate Similarity	NPD7507	Approved
0.7174	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6928	Phase 2
0.7025	Intermediate Similarity	NPD7319	Approved
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.6991	Remote Similarity	NPD8133	Approved
0.6939	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4225	Approved
0.6837	Remote Similarity	NPD6695	Phase 3
0.6827	Remote Similarity	NPD7748	Approved
0.681	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6370	Approved
0.6803	Remote Similarity	NPD7736	Approved
0.6796	Remote Similarity	NPD7515	Phase 2
0.6792	Remote Similarity	NPD7902	Approved
0.6771	Remote Similarity	NPD6929	Approved
0.6768	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4786	Approved
0.675	Remote Similarity	NPD8328	Phase 3
0.675	Remote Similarity	NPD6067	Discontinued
0.6735	Remote Similarity	NPD3667	Approved
0.6731	Remote Similarity	NPD6399	Phase 3
0.6723	Remote Similarity	NPD8516	Approved
0.6723	Remote Similarity	NPD8515	Approved
0.6723	Remote Similarity	NPD8517	Approved
0.6723	Remote Similarity	NPD8513	Phase 3
0.6702	Remote Similarity	NPD8264	Approved
0.6701	Remote Similarity	NPD6931	Approved
0.6701	Remote Similarity	NPD6930	Phase 2
0.6639	Remote Similarity	NPD6059	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6637	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3618	Phase 1
0.6602	Remote Similarity	NPD6051	Approved
0.6602	Remote Similarity	NPD5328	Approved
0.6596	Remote Similarity	NPD6926	Approved
0.6596	Remote Similarity	NPD6924	Approved
0.6585	Remote Similarity	NPD8293	Discontinued
0.6571	Remote Similarity	NPD8171	Discontinued
0.6569	Remote Similarity	NPD7750	Discontinued
0.6569	Remote Similarity	NPD7524	Approved
0.6562	Remote Similarity	NPD5776	Phase 2
0.6562	Remote Similarity	NPD6925	Approved
0.6535	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7514	Phase 3
0.6531	Remote Similarity	NPD7332	Phase 2
0.6531	Remote Similarity	NPD7509	Discontinued
0.6525	Remote Similarity	NPD7115	Discovery
0.6509	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7900	Approved
0.6495	Remote Similarity	NPD7145	Approved
0.6476	Remote Similarity	NPD8034	Phase 2
0.6476	Remote Similarity	NPD6079	Approved
0.6476	Remote Similarity	NPD8035	Phase 2
0.6466	Remote Similarity	NPD6882	Approved
0.6465	Remote Similarity	NPD6902	Approved
0.6458	Remote Similarity	NPD6933	Approved
0.6455	Remote Similarity	NPD5344	Discontinued
0.6455	Remote Similarity	NPD4159	Approved
0.6446	Remote Similarity	NPD6016	Approved
0.6446	Remote Similarity	NPD6015	Approved
0.6435	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7492	Approved
0.6421	Remote Similarity	NPD4784	Approved
0.6421	Remote Similarity	NPD4785	Approved
0.6415	Remote Similarity	NPD4202	Approved
0.6393	Remote Similarity	NPD5988	Approved
0.6392	Remote Similarity	NPD6932	Approved
0.6387	Remote Similarity	NPD6009	Approved
0.6383	Remote Similarity	NPD7152	Approved
0.6383	Remote Similarity	NPD7151	Approved
0.6383	Remote Similarity	NPD4243	Approved
0.6383	Remote Similarity	NPD7150	Approved
0.6373	Remote Similarity	NPD6893	Approved
0.6372	Remote Similarity	NPD7128	Approved
0.6372	Remote Similarity	NPD5739	Approved
0.6372	Remote Similarity	NPD6402	Approved
0.6372	Remote Similarity	NPD6008	Approved
0.6372	Remote Similarity	NPD6675	Approved
0.6371	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD4748	Discontinued
0.6346	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6922	Approved
0.6344	Remote Similarity	NPD6923	Approved
0.6328	Remote Similarity	NPD8449	Approved
0.6327	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7087	Discontinued
0.6321	Remote Similarity	NPD7637	Suspended
0.632	Remote Similarity	NPD7078	Approved
0.63	Remote Similarity	NPD6898	Phase 1
0.6279	Remote Similarity	NPD8450	Suspended
0.6277	Remote Similarity	NPD7143	Approved
0.6277	Remote Similarity	NPD7144	Approved
0.6275	Remote Similarity	NPD3133	Approved
0.6275	Remote Similarity	NPD3666	Approved
0.6275	Remote Similarity	NPD3665	Phase 1
0.627	Remote Similarity	NPD6033	Approved
0.6263	Remote Similarity	NPD6683	Phase 2
0.6261	Remote Similarity	NPD7320	Approved
0.6261	Remote Similarity	NPD6881	Approved
0.6261	Remote Similarity	NPD6899	Approved
0.6239	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD3168	Discontinued
0.6216	Remote Similarity	NPD6648	Approved
0.6214	Remote Similarity	NPD1694	Approved
0.6207	Remote Similarity	NPD6373	Approved
0.6207	Remote Similarity	NPD6372	Approved
0.6204	Remote Similarity	NPD7625	Phase 1
0.6186	Remote Similarity	NPD6053	Discontinued
0.6182	Remote Similarity	NPD4755	Approved
0.6174	Remote Similarity	NPD5697	Approved
0.6174	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD7521	Approved
0.6154	Remote Similarity	NPD7334	Approved
0.6154	Remote Similarity	NPD6409	Approved
0.6154	Remote Similarity	NPD7146	Approved
0.6154	Remote Similarity	NPD5330	Approved
0.6154	Remote Similarity	NPD6684	Approved
0.6154	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6134	Remote Similarity	NPD4632	Approved
0.6129	Remote Similarity	NPD5125	Phase 3
0.6129	Remote Similarity	NPD5126	Approved
0.6126	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6011	Approved
0.6117	Remote Similarity	NPD3668	Phase 3
0.6111	Remote Similarity	NPD5779	Approved
0.6111	Remote Similarity	NPD5778	Approved
0.6111	Remote Similarity	NPD368	Approved
0.6106	Remote Similarity	NPD5211	Phase 2
0.6102	Remote Similarity	NPD8130	Phase 1
0.6102	Remote Similarity	NPD6617	Approved
0.6102	Remote Similarity	NPD6649	Approved
0.6102	Remote Similarity	NPD6847	Approved
0.6102	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6650	Approved
0.6102	Remote Similarity	NPD6869	Approved
0.6091	Remote Similarity	NPD5222	Approved
0.6091	Remote Similarity	NPD5221	Approved
0.6091	Remote Similarity	NPD4697	Phase 3
0.6091	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD1810	Approved
0.6082	Remote Similarity	NPD1811	Approved
0.6078	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD4700	Approved
0.6071	Remote Similarity	NPD5285	Approved
0.6071	Remote Similarity	NPD4696	Approved
0.6071	Remote Similarity	NPD5286	Approved
0.6068	Remote Similarity	NPD6013	Approved
0.6068	Remote Similarity	NPD6014	Approved
0.6068	Remote Similarity	NPD6012	Approved
0.6063	Remote Similarity	NPD8074	Phase 3
0.605	Remote Similarity	NPD8297	Approved
0.6038	Remote Similarity	NPD6903	Approved
0.6036	Remote Similarity	NPD5173	Approved
0.6036	Remote Similarity	NPD6084	Phase 2
0.6036	Remote Similarity	NPD6083	Phase 2
0.602	Remote Similarity	NPD4190	Phase 3
0.602	Remote Similarity	NPD5275	Approved
0.6019	Remote Similarity	NPD6411	Approved
0.6018	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7991	Discontinued
0.6	Remote Similarity	NPD5141	Approved
0.5982	Remote Similarity	NPD5290	Discontinued
0.5968	Remote Similarity	NPD6319	Approved
0.5968	Remote Similarity	NPD7741	Discontinued
0.5965	Remote Similarity	NPD5225	Approved
0.5965	Remote Similarity	NPD4633	Approved
0.5965	Remote Similarity	NPD5226	Approved
0.5965	Remote Similarity	NPD5224	Approved
0.5952	Remote Similarity	NPD7604	Phase 2
0.5948	Remote Similarity	NPD6640	Phase 3
0.5943	Remote Similarity	NPD3573	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