NPASS Compound

Structure

NPC151477 OpenBabel07101718202D 21 22 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 16 1 0 0 0 0 11 19 2 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 14 3 1 1 0 0 0 15 4 1 1 0 0 0 15 18 1 0 0 0 0 16 20 2 0 0 0 0 17 14 1 6 0 0 0 17 19 1 0 0 0 0 18 19 1 0 0 0 0 20 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	335.608
LogP:	6.779
LogD:	5.084
LogS:	-6.028
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	3.79
Fsp3:	0.6
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:	-4.729
MDCK Permeability:	1.213459745486034e-05
Pgp-inhibitor:	0.863
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.446
Plasma Protein Binding (PPB):	98.99038696289062%
Volume Distribution (VD):	8.113
Pgp-substrate:	3.655839443206787%

ADMET: Metabolism

CYP1A2-inhibitor:	0.883
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.779
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.691
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.642
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.777
CYP3A4-substrate:	0.523

ADMET: Excretion

Clearance (CL):	14.837
Half-life (T1/2):	0.097

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.763
Drug-inuced Liver Injury (DILI):	0.489
AMES Toxicity:	0.234
Rat Oral Acute Toxicity:	0.15
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.809
Carcinogencity:	0.162
Eye Corrosion:	0.144
Eye Irritation:	0.969
Respiratory Toxicity:	0.569

Download Data

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

Natural Product: NPC151477

Natural Product ID:	NPC151477
*Common Name:**	7-Hydroxyerogorgiaene
IUPAC Name:	(5R,8S)-3,8-dimethyl-5-[(2S)-6-methylhept-5-en-2-yl]-5,6,7,8-tetrahydronaphthalen-2-ol
Synonyms:	7-Hydroxyerogorgiaene
Standard InCHIKey:	HWRNTAPYVJUXEL-YQQAZPJKSA-N
Standard InCHI:	InChI=1S/C20H30O/c1-13(2)7-6-8-14(3)17-10-9-15(4)18-12-20(21)16(5)11-19(17)18/h7,11-12,14-15,17,21H,6,8-10H2,1-5H3/t14-,15-,17+/m0/s1
SMILES:	CC(=CCC[C@H](C)[C@H]1CC[C@H](C)c2cc(c(C)cc12)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477696
PubChem CID:	3001918
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000351] Biflorane and serrulatane diterpenoids

*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
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[10425124]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10822593]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	West Indian sea	n.a.	PMID[11170678]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828474]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	Colombian	n.a.	PMID[15497938]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17715964]
NPO31261	Pseudopterogorgia elisabethae	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21978379]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Activity	=	77.0	%	PMID[516378]

☑ 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 NPC151477 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	344
0.1-0.2	1904
0.2-0.3	4788
0.3-0.4	12761
0.4-0.5	7118
0.5-0.6	9176
0.6-0.7	4997
0.7-0.8	1251
0.8-0.85	236
0.85-0.9	95
0.9-0.95	23
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9798	High Similarity	NPC117115
0.97	High Similarity	NPC21594
0.9612	High Similarity	NPC260323
0.9612	High Similarity	NPC176279
0.9608	High Similarity	NPC58865
0.9519	High Similarity	NPC250323
0.9429	High Similarity	NPC715
0.9423	High Similarity	NPC151537
0.934	High Similarity	NPC195922
0.9333	High Similarity	NPC46940
0.9327	High Similarity	NPC141782
0.9327	High Similarity	NPC132720
0.9327	High Similarity	NPC13482
0.9252	High Similarity	NPC192948
0.9252	High Similarity	NPC35797
0.9238	High Similarity	NPC95716
0.9167	High Similarity	NPC38893
0.9167	High Similarity	NPC471668
0.9167	High Similarity	NPC308311
0.9167	High Similarity	NPC477137
0.9151	High Similarity	NPC471179
0.9135	High Similarity	NPC11554
0.9118	High Similarity	NPC238696
0.9083	High Similarity	NPC304510
0.9083	High Similarity	NPC477136
0.9083	High Similarity	NPC172219
0.9048	High Similarity	NPC314187
0.901	High Similarity	NPC211885
0.9	High Similarity	NPC6597
0.9	High Similarity	NPC79241
0.9	High Similarity	NPC471671
0.9	High Similarity	NPC77492
0.8991	High Similarity	NPC219112
0.8981	High Similarity	NPC268160
0.8942	High Similarity	NPC271274
0.8932	High Similarity	NPC272029
0.8919	High Similarity	NPC93071
0.8919	High Similarity	NPC469644
0.8919	High Similarity	NPC151197
0.8919	High Similarity	NPC126002
0.89	High Similarity	NPC259512
0.89	High Similarity	NPC312132
0.8899	High Similarity	NPC147179
0.8889	High Similarity	NPC317869
0.8889	High Similarity	NPC322239
0.8889	High Similarity	NPC263753
0.8879	High Similarity	NPC469912
0.8879	High Similarity	NPC322753
0.8846	High Similarity	NPC138942
0.8839	High Similarity	NPC478121
0.8835	High Similarity	NPC168829
0.8829	High Similarity	NPC154030
0.8824	High Similarity	NPC72729
0.8824	High Similarity	NPC225506
0.8818	High Similarity	NPC469663
0.8818	High Similarity	NPC308828
0.8818	High Similarity	NPC92
0.8807	High Similarity	NPC107240
0.88	High Similarity	NPC8392
0.8796	High Similarity	NPC228425
0.8785	High Similarity	NPC224870
0.8785	High Similarity	NPC296683
0.8761	High Similarity	NPC32322
0.8761	High Similarity	NPC241001
0.8761	High Similarity	NPC259703
0.875	High Similarity	NPC288411
0.8739	High Similarity	NPC299180
0.8739	High Similarity	NPC16030
0.8738	High Similarity	NPC252105
0.8727	High Similarity	NPC469719
0.8725	High Similarity	NPC252821
0.8725	High Similarity	NPC122005
0.8725	High Similarity	NPC299762
0.8725	High Similarity	NPC33675
0.8716	High Similarity	NPC117846
0.8704	High Similarity	NPC77772
0.8704	High Similarity	NPC266937
0.8704	High Similarity	NPC470770
0.87	High Similarity	NPC245187
0.8684	High Similarity	NPC249340
0.8684	High Similarity	NPC154696
0.8684	High Similarity	NPC162935
0.8679	High Similarity	NPC320439
0.8661	High Similarity	NPC469609
0.8627	High Similarity	NPC32674
0.8627	High Similarity	NPC156313
0.8624	High Similarity	NPC177962
0.8624	High Similarity	NPC62867
0.8624	High Similarity	NPC302371
0.8614	High Similarity	NPC144682
0.8614	High Similarity	NPC222146
0.8609	High Similarity	NPC121168
0.8609	High Similarity	NPC297057
0.8609	High Similarity	NPC11250
0.8596	High Similarity	NPC129176
0.8585	High Similarity	NPC54765
0.8571	High Similarity	NPC475225
0.8559	High Similarity	NPC246760
0.8559	High Similarity	NPC84999
0.8558	High Similarity	NPC51015
0.8558	High Similarity	NPC477685
0.8545	High Similarity	NPC321589
0.8534	High Similarity	NPC471187
0.8532	High Similarity	NPC470723
0.8532	High Similarity	NPC165770
0.8532	High Similarity	NPC4493
0.8532	High Similarity	NPC224527
0.8532	High Similarity	NPC225679
0.8532	High Similarity	NPC476632
0.8529	High Similarity	NPC216520
0.8529	High Similarity	NPC132271
0.8529	High Similarity	NPC292730
0.8529	High Similarity	NPC473388
0.8529	High Similarity	NPC82664
0.8519	High Similarity	NPC186385
0.8519	High Similarity	NPC299568
0.8515	High Similarity	NPC76938
0.8509	High Similarity	NPC260832
0.8509	High Similarity	NPC135467
0.85	High Similarity	NPC204210
0.85	High Similarity	NPC231150
0.85	High Similarity	NPC304541
0.8496	Intermediate Similarity	NPC206
0.8491	Intermediate Similarity	NPC47284
0.8491	Intermediate Similarity	NPC219286
0.8491	Intermediate Similarity	NPC99557
0.8485	Intermediate Similarity	NPC70436
0.8482	Intermediate Similarity	NPC115808
0.8482	Intermediate Similarity	NPC154511
0.8482	Intermediate Similarity	NPC474358
0.8482	Intermediate Similarity	NPC474387
0.8482	Intermediate Similarity	NPC247858
0.8482	Intermediate Similarity	NPC141001
0.8482	Intermediate Similarity	NPC137496
0.8482	Intermediate Similarity	NPC257540
0.8476	Intermediate Similarity	NPC235762
0.8476	Intermediate Similarity	NPC471228
0.8476	Intermediate Similarity	NPC108497
0.8476	Intermediate Similarity	NPC269212
0.8468	Intermediate Similarity	NPC471534
0.8468	Intermediate Similarity	NPC249270
0.8462	Intermediate Similarity	NPC199273
0.8462	Intermediate Similarity	NPC181334
0.8455	Intermediate Similarity	NPC43525
0.8455	Intermediate Similarity	NPC166995
0.8448	Intermediate Similarity	NPC71094
0.8448	Intermediate Similarity	NPC176208
0.8447	Intermediate Similarity	NPC225464
0.8431	Intermediate Similarity	NPC32714
0.8431	Intermediate Similarity	NPC274678
0.8431	Intermediate Similarity	NPC26244
0.8426	Intermediate Similarity	NPC95344
0.8426	Intermediate Similarity	NPC64586
0.8426	Intermediate Similarity	NPC262365
0.8421	Intermediate Similarity	NPC176893
0.8416	Intermediate Similarity	NPC3358
0.8416	Intermediate Similarity	NPC306884
0.8416	Intermediate Similarity	NPC94139
0.8416	Intermediate Similarity	NPC210497
0.8416	Intermediate Similarity	NPC147284
0.8416	Intermediate Similarity	NPC162314
0.8411	Intermediate Similarity	NPC469913
0.8411	Intermediate Similarity	NPC53740
0.8407	Intermediate Similarity	NPC470760
0.84	Intermediate Similarity	NPC192
0.8396	Intermediate Similarity	NPC254965
0.8396	Intermediate Similarity	NPC327811
0.8396	Intermediate Similarity	NPC475580
0.8393	Intermediate Similarity	NPC474486
0.839	Intermediate Similarity	NPC137750
0.839	Intermediate Similarity	NPC124030
0.8384	Intermediate Similarity	NPC19680
0.8381	Intermediate Similarity	NPC12221
0.8378	Intermediate Similarity	NPC23804
0.8365	Intermediate Similarity	NPC128723
0.8365	Intermediate Similarity	NPC92730
0.8362	Intermediate Similarity	NPC474115
0.8362	Intermediate Similarity	NPC253627
0.835	Intermediate Similarity	NPC202986
0.8349	Intermediate Similarity	NPC254833
0.8349	Intermediate Similarity	NPC19808
0.8349	Intermediate Similarity	NPC33728
0.8349	Intermediate Similarity	NPC228343
0.8348	Intermediate Similarity	NPC103916
0.8333	Intermediate Similarity	NPC66834
0.8333	Intermediate Similarity	NPC128062
0.8333	Intermediate Similarity	NPC48342
0.8333	Intermediate Similarity	NPC152415
0.8333	Intermediate Similarity	NPC164649
0.8333	Intermediate Similarity	NPC289769
0.8333	Intermediate Similarity	NPC27323
0.8333	Intermediate Similarity	NPC151715
0.8333	Intermediate Similarity	NPC328694
0.8333	Intermediate Similarity	NPC316301
0.8319	Intermediate Similarity	NPC100414
0.8319	Intermediate Similarity	NPC312105
0.8319	Intermediate Similarity	NPC261973
0.8319	Intermediate Similarity	NPC325294
0.8319	Intermediate Similarity	NPC43000
0.8319	Intermediate Similarity	NPC321822

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 NPC151477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	1028
0.2-0.3	1392
0.3-0.4	2987
0.4-0.5	1803
0.5-0.6	1105
0.6-0.7	372
0.7-0.8	80
0.8-0.85	12
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8972	High Similarity	NPD7635	Approved
0.89	High Similarity	NPD288	Approved
0.8857	High Similarity	NPD2342	Discontinued
0.88	High Similarity	NPD844	Approved
0.8725	High Similarity	NPD3020	Approved
0.8614	High Similarity	NPD1809	Phase 2
0.86	High Similarity	NPD845	Approved
0.8519	High Similarity	NPD4750	Phase 3
0.8431	Intermediate Similarity	NPD2860	Approved
0.8431	Intermediate Similarity	NPD2859	Approved
0.8349	Intermediate Similarity	NPD3021	Approved
0.8349	Intermediate Similarity	NPD3022	Approved
0.8333	Intermediate Similarity	NPD3091	Approved
0.8333	Intermediate Similarity	NPD2934	Approved
0.8333	Intermediate Similarity	NPD2933	Approved
0.8333	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.822	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD3019	Approved
0.819	Intermediate Similarity	NPD2932	Approved
0.819	Intermediate Similarity	NPD4059	Approved
0.8113	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD4093	Discontinued
0.8051	Intermediate Similarity	NPD3092	Approved
0.8034	Intermediate Similarity	NPD4626	Approved
0.8034	Intermediate Similarity	NPD1751	Approved
0.8034	Intermediate Similarity	NPD2286	Discontinued
0.8018	Intermediate Similarity	NPD1792	Phase 2
0.8	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3095	Discontinued
0.787	Intermediate Similarity	NPD846	Approved
0.787	Intermediate Similarity	NPD940	Approved
0.7863	Intermediate Similarity	NPD5304	Approved
0.7863	Intermediate Similarity	NPD5303	Approved
0.7826	Intermediate Similarity	NPD497	Approved
0.78	Intermediate Similarity	NPD111	Approved
0.7798	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD3094	Phase 2
0.7748	Intermediate Similarity	NPD1445	Approved
0.7748	Intermediate Similarity	NPD1444	Approved
0.7739	Intermediate Similarity	NPD498	Approved
0.7739	Intermediate Similarity	NPD2234	Approved
0.7739	Intermediate Similarity	NPD495	Approved
0.7739	Intermediate Similarity	NPD496	Approved
0.7739	Intermediate Similarity	NPD2228	Approved
0.7739	Intermediate Similarity	NPD2229	Approved
0.7731	Intermediate Similarity	NPD4589	Approved
0.7724	Intermediate Similarity	NPD2194	Approved
0.7724	Intermediate Similarity	NPD2195	Approved
0.7719	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7340	Approved
0.768	Intermediate Similarity	NPD4625	Phase 3
0.7661	Intermediate Similarity	NPD3635	Approved
0.7661	Intermediate Similarity	NPD3636	Approved
0.7661	Intermediate Similarity	NPD5736	Approved
0.7661	Intermediate Similarity	NPD3637	Approved
0.7656	Intermediate Similarity	NPD4097	Suspended
0.7647	Intermediate Similarity	NPD5691	Approved
0.7638	Intermediate Similarity	NPD4060	Phase 1
0.7615	Intermediate Similarity	NPD1242	Phase 1
0.76	Intermediate Similarity	NPD2605	Approved
0.76	Intermediate Similarity	NPD2606	Approved
0.7586	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD1398	Phase 1
0.7561	Intermediate Similarity	NPD6696	Suspended
0.7561	Intermediate Similarity	NPD1283	Approved
0.754	Intermediate Similarity	NPD5156	Approved
0.754	Intermediate Similarity	NPD5155	Approved
0.7521	Intermediate Similarity	NPD3026	Approved
0.7521	Intermediate Similarity	NPD3023	Approved
0.75	Intermediate Similarity	NPD3025	Approved
0.75	Intermediate Similarity	NPD1651	Approved
0.75	Intermediate Similarity	NPD3024	Approved
0.748	Intermediate Similarity	NPD4749	Approved
0.7477	Intermediate Similarity	NPD9500	Approved
0.746	Intermediate Similarity	NPD3594	Approved
0.746	Intermediate Similarity	NPD3595	Approved
0.7459	Intermediate Similarity	NPD1201	Approved
0.7458	Intermediate Similarity	NPD6671	Approved
0.744	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD4624	Approved
0.7422	Intermediate Similarity	NPD6663	Approved
0.7364	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD3620	Phase 2
0.736	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1281	Approved
0.7297	Intermediate Similarity	NPD3028	Approved
0.7288	Intermediate Similarity	NPD5283	Phase 1
0.7288	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7330	Discontinued
0.7258	Intermediate Similarity	NPD2233	Approved
0.7258	Intermediate Similarity	NPD2230	Approved
0.7258	Intermediate Similarity	NPD2232	Approved
0.7244	Intermediate Similarity	NPD2861	Phase 2
0.7222	Intermediate Similarity	NPD1470	Approved
0.7218	Intermediate Similarity	NPD5408	Approved
0.7218	Intermediate Similarity	NPD5404	Approved
0.7218	Intermediate Similarity	NPD5405	Approved
0.7218	Intermediate Similarity	NPD5406	Approved
0.7213	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1669	Approved
0.72	Intermediate Similarity	NPD5327	Phase 3
0.7197	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1611	Approved
0.7167	Intermediate Similarity	NPD709	Approved
0.7143	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7743	Approved
0.7143	Intermediate Similarity	NPD7742	Approved
0.7119	Intermediate Similarity	NPD228	Approved
0.7107	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9610	Approved
0.7105	Intermediate Similarity	NPD9608	Approved
0.7101	Intermediate Similarity	NPD7390	Discontinued
0.7099	Intermediate Similarity	NPD4140	Approved
0.7097	Intermediate Similarity	NPD1983	Approved
0.7097	Intermediate Similarity	NPD2688	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1981	Approved
0.7097	Intermediate Similarity	NPD3143	Discontinued
0.7097	Intermediate Similarity	NPD1980	Approved
0.7083	Intermediate Similarity	NPD1793	Approved
0.7083	Intermediate Similarity	NPD1791	Approved
0.7083	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4908	Phase 1
0.705	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5735	Approved
0.704	Intermediate Similarity	NPD1610	Phase 2
0.7037	Intermediate Similarity	NPD4721	Approved
0.7037	Intermediate Similarity	NPD4726	Approved
0.7037	Intermediate Similarity	NPD4725	Approved
0.7016	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2667	Approved
0.7016	Intermediate Similarity	NPD2668	Approved
0.7007	Intermediate Similarity	NPD7003	Approved
0.6992	Remote Similarity	NPD2157	Approved
0.6992	Remote Similarity	NPD6353	Approved
0.6985	Remote Similarity	NPD4256	Phase 2
0.6985	Remote Similarity	NPD4257	Approved
0.6984	Remote Similarity	NPD3070	Discontinued
0.6978	Remote Similarity	NPD2421	Approved
0.6978	Remote Similarity	NPD2420	Approved
0.6978	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7041	Phase 2
0.697	Remote Similarity	NPD2979	Phase 3
0.6967	Remote Similarity	NPD7636	Approved
0.6963	Remote Similarity	NPD6099	Approved
0.6963	Remote Similarity	NPD6100	Approved
0.6953	Remote Similarity	NPD1164	Approved
0.6947	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2211	Approved
0.6934	Remote Similarity	NPD2209	Approved
0.6934	Remote Similarity	NPD3638	Discontinued
0.6917	Remote Similarity	NPD9379	Approved
0.6917	Remote Similarity	NPD9377	Approved
0.6911	Remote Similarity	NPD7644	Approved
0.6899	Remote Similarity	NPD6584	Phase 3
0.6885	Remote Similarity	NPD6387	Discontinued
0.6879	Remote Similarity	NPD6090	Discontinued
0.6866	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2684	Approved
0.6861	Remote Similarity	NPD7037	Approved
0.6846	Remote Similarity	NPD4208	Discontinued
0.6842	Remote Similarity	NPD1616	Discontinued
0.6842	Remote Similarity	NPD2238	Phase 2
0.6838	Remote Similarity	NPD2935	Discontinued
0.6835	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3055	Approved
0.6822	Remote Similarity	NPD3053	Approved
0.6814	Remote Similarity	NPD9273	Approved
0.6812	Remote Similarity	NPD6674	Discontinued
0.6807	Remote Similarity	NPD5451	Approved
0.6803	Remote Similarity	NPD475	Phase 2
0.6803	Remote Similarity	NPD5951	Approved
0.68	Remote Similarity	NPD3443	Approved
0.68	Remote Similarity	NPD3445	Approved
0.68	Remote Similarity	NPD3444	Approved
0.6797	Remote Similarity	NPD4659	Approved
0.6788	Remote Similarity	NPD5762	Approved
0.6788	Remote Similarity	NPD5763	Approved
0.6788	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4817	Approved
0.6783	Remote Similarity	NPD4818	Approved
0.6777	Remote Similarity	NPD1138	Approved
0.6767	Remote Similarity	NPD6407	Approved
0.6767	Remote Similarity	NPD8032	Phase 2
0.6767	Remote Similarity	NPD6405	Approved
0.6765	Remote Similarity	NPD4108	Discontinued
0.6763	Remote Similarity	NPD8166	Discontinued
0.6748	Remote Similarity	NPD7157	Approved
0.6744	Remote Similarity	NPD5310	Approved
0.6744	Remote Similarity	NPD5311	Approved
0.6742	Remote Similarity	NPD3027	Phase 3
0.672	Remote Similarity	NPD1548	Phase 1

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