NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.23
Volume:	326.817
LogP:	7.235
LogD:	5.484
LogS:	-6.77
# Rotatable Bonds:	4
TPSA:	0.0
# H-Bond Aceptor:	0
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	0

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	3.579
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:	-4.598
MDCK Permeability:	9.47869284573244e-06
Pgp-inhibitor:	0.957
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.168
Plasma Protein Binding (PPB):	98.6075210571289%
Volume Distribution (VD):	6.382
Pgp-substrate:	3.5141184329986572%

ADMET: Metabolism

CYP1A2-inhibitor:	0.686
CYP1A2-substrate:	0.907
CYP2C19-inhibitor:	0.68
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.643
CYP2C9-substrate:	0.811
CYP2D6-inhibitor:	0.302
CYP2D6-substrate:	0.74
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.645

ADMET: Excretion

Clearance (CL):	10.954
Half-life (T1/2):	0.043

ADMET: Toxicity

hERG Blockers:	0.228
Human Hepatotoxicity (H-HT):	0.738
Drug-inuced Liver Injury (DILI):	0.641
AMES Toxicity:	0.378
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.568
Skin Sensitization:	0.933
Carcinogencity:	0.189
Eye Corrosion:	0.48
Eye Irritation:	0.973
Respiratory Toxicity:	0.078

Download Data

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

Natural Product: NPC54269

Natural Product ID:	NPC54269
*Common Name:**	Erogorgiaene
IUPAC Name:	(1S,4R)-1,6-dimethyl-4-[(2S)-6-methylhept-5-en-2-yl]-1,2,3,4-tetrahydronaphthalene
Synonyms:	Erogorgiaene
Standard InCHIKey:	JWQVCYABIGUFIY-JENIJYKNSA-N
Standard InCHI:	InChI=1S/C20H30/c1-14(2)7-6-8-16(4)19-12-10-17(5)18-11-9-15(3)13-20(18)19/h7,9,11,13,16-17,19H,6,8,10,12H2,1-5H3/t16-,17-,19+/m0/s1
SMILES:	CC(=CCC[C@H](C)[C@H]1CC[C@H](C)c2ccc(C)cc12)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507106
PubChem CID:	9816893
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	=	96.0	%	PMID[479235]

☑ 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 NPC54269 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	944
0.1-0.2	2638
0.2-0.3	12485
0.3-0.4	17541
0.4-0.5	7342
0.5-0.6	1308
0.6-0.7	305
0.7-0.8	77
0.8-0.85	21
0.85-0.9	16
0.9-0.95	19
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9437	High Similarity	NPC3190
0.9437	High Similarity	NPC249018
0.9275	High Similarity	NPC135433
0.9275	High Similarity	NPC158028
0.9275	High Similarity	NPC280135
0.9275	High Similarity	NPC193578
0.9275	High Similarity	NPC226999
0.9275	High Similarity	NPC1008
0.9275	High Similarity	NPC39799
0.9275	High Similarity	NPC87099
0.9254	High Similarity	NPC6107
0.9178	High Similarity	NPC159661
0.9104	High Similarity	NPC113837
0.9104	High Similarity	NPC289915
0.8986	High Similarity	NPC246822
0.8986	High Similarity	NPC213570
0.8986	High Similarity	NPC139416
0.8955	High Similarity	NPC198023
0.8955	High Similarity	NPC155172
0.8955	High Similarity	NPC32312
0.8889	High Similarity	NPC307195
0.8806	High Similarity	NPC45756
0.8806	High Similarity	NPC88566
0.88	High Similarity	NPC315216
0.875	High Similarity	NPC96835
0.875	High Similarity	NPC258492
0.8696	High Similarity	NPC267443
0.8657	High Similarity	NPC71009
0.8592	High Similarity	NPC72670
0.8592	High Similarity	NPC251490
0.8551	High Similarity	NPC178527
0.8533	High Similarity	NPC245896
0.8533	High Similarity	NPC66270
0.8507	High Similarity	NPC135924
0.8507	High Similarity	NPC310758
0.8507	High Similarity	NPC150196
0.8507	High Similarity	NPC248705
0.8507	High Similarity	NPC210849
0.8507	High Similarity	NPC238023
0.8507	High Similarity	NPC54368
0.8406	Intermediate Similarity	NPC291066
0.8382	Intermediate Similarity	NPC22786
0.8358	Intermediate Similarity	NPC147062
0.8356	Intermediate Similarity	NPC1901
0.8312	Intermediate Similarity	NPC50063
0.8272	Intermediate Similarity	NPC60408
0.8267	Intermediate Similarity	NPC110264
0.8261	Intermediate Similarity	NPC113670
0.8235	Intermediate Similarity	NPC246588
0.8209	Intermediate Similarity	NPC8235
0.8209	Intermediate Similarity	NPC64270
0.8205	Intermediate Similarity	NPC242628
0.8116	Intermediate Similarity	NPC29680
0.8116	Intermediate Similarity	NPC66517
0.8082	Intermediate Similarity	NPC263385
0.8072	Intermediate Similarity	NPC298115
0.806	Intermediate Similarity	NPC300345
0.806	Intermediate Similarity	NPC120441
0.806	Intermediate Similarity	NPC212114
0.806	Intermediate Similarity	NPC65873
0.8052	Intermediate Similarity	NPC255345
0.8	Intermediate Similarity	NPC21211
0.7976	Intermediate Similarity	NPC26224
0.7941	Intermediate Similarity	NPC36357
0.7941	Intermediate Similarity	NPC114327
0.791	Intermediate Similarity	NPC269586
0.791	Intermediate Similarity	NPC198841
0.7901	Intermediate Similarity	NPC267704
0.7882	Intermediate Similarity	NPC220596
0.7882	Intermediate Similarity	NPC125226
0.7761	Intermediate Similarity	NPC149436
0.7761	Intermediate Similarity	NPC277704
0.7703	Intermediate Similarity	NPC473206
0.7606	Intermediate Similarity	NPC200745
0.7595	Intermediate Similarity	NPC103488
0.7586	Intermediate Similarity	NPC323420
0.7586	Intermediate Similarity	NPC153885
0.7571	Intermediate Similarity	NPC169110
0.7528	Intermediate Similarity	NPC185208
0.7528	Intermediate Similarity	NPC219573
0.75	Intermediate Similarity	NPC238219
0.7471	Intermediate Similarity	NPC133461
0.747	Intermediate Similarity	NPC133162
0.7467	Intermediate Similarity	NPC297358
0.7467	Intermediate Similarity	NPC200936
0.7444	Intermediate Similarity	NPC324602
0.7444	Intermediate Similarity	NPC239185
0.7444	Intermediate Similarity	NPC226041
0.7416	Intermediate Similarity	NPC260233
0.7407	Intermediate Similarity	NPC17408
0.7407	Intermediate Similarity	NPC157055
0.7407	Intermediate Similarity	NPC285716
0.7386	Intermediate Similarity	NPC155232
0.7363	Intermediate Similarity	NPC49994
0.7363	Intermediate Similarity	NPC134882
0.7356	Intermediate Similarity	NPC277277
0.7333	Intermediate Similarity	NPC22760
0.7297	Intermediate Similarity	NPC36440
0.7294	Intermediate Similarity	NPC307
0.7294	Intermediate Similarity	NPC160339
0.7283	Intermediate Similarity	NPC221825
0.7253	Intermediate Similarity	NPC265220
0.725	Intermediate Similarity	NPC9796
0.7229	Intermediate Similarity	NPC230068
0.7215	Intermediate Similarity	NPC276699
0.7204	Intermediate Similarity	NPC136810
0.7204	Intermediate Similarity	NPC128248
0.7204	Intermediate Similarity	NPC476993
0.7204	Intermediate Similarity	NPC225079
0.7204	Intermediate Similarity	NPC133809
0.7204	Intermediate Similarity	NPC109514
0.7191	Intermediate Similarity	NPC59677
0.7191	Intermediate Similarity	NPC188844
0.7191	Intermediate Similarity	NPC314690
0.7191	Intermediate Similarity	NPC1682
0.7179	Intermediate Similarity	NPC212463
0.7174	Intermediate Similarity	NPC75724
0.7162	Intermediate Similarity	NPC264470
0.7159	Intermediate Similarity	NPC173413
0.7126	Intermediate Similarity	NPC153308
0.7111	Intermediate Similarity	NPC289883
0.7093	Intermediate Similarity	NPC164526
0.7079	Intermediate Similarity	NPC284475
0.7079	Intermediate Similarity	NPC475023
0.7079	Intermediate Similarity	NPC103346
0.7079	Intermediate Similarity	NPC475059
0.7073	Intermediate Similarity	NPC272260
0.7059	Intermediate Similarity	NPC95429
0.7053	Intermediate Similarity	NPC19856
0.7037	Intermediate Similarity	NPC298023
0.7037	Intermediate Similarity	NPC290638
0.7027	Intermediate Similarity	NPC50266
0.7013	Intermediate Similarity	NPC5324
0.7011	Intermediate Similarity	NPC69057
0.7	Intermediate Similarity	NPC475057
0.7	Intermediate Similarity	NPC128645
0.6988	Remote Similarity	NPC164449
0.6988	Remote Similarity	NPC477703
0.6988	Remote Similarity	NPC184030
0.6986	Remote Similarity	NPC45255
0.6979	Remote Similarity	NPC56168
0.6979	Remote Similarity	NPC472222
0.6979	Remote Similarity	NPC472221
0.6951	Remote Similarity	NPC224544
0.6941	Remote Similarity	NPC477770
0.6932	Remote Similarity	NPC267262
0.6932	Remote Similarity	NPC157778
0.6923	Remote Similarity	NPC95289
0.6907	Remote Similarity	NPC471186
0.6907	Remote Similarity	NPC243601
0.6889	Remote Similarity	NPC470926
0.6883	Remote Similarity	NPC311343
0.6875	Remote Similarity	NPC247976
0.6867	Remote Similarity	NPC139901
0.6867	Remote Similarity	NPC151405
0.6854	Remote Similarity	NPC325709
0.6854	Remote Similarity	NPC199567
0.6854	Remote Similarity	NPC418308
0.6849	Remote Similarity	NPC147578
0.6848	Remote Similarity	NPC472880
0.6842	Remote Similarity	NPC245927
0.6837	Remote Similarity	NPC142326
0.6837	Remote Similarity	NPC94751
0.6835	Remote Similarity	NPC74458
0.6829	Remote Similarity	NPC179726
0.6824	Remote Similarity	NPC121478
0.6824	Remote Similarity	NPC73637
0.6818	Remote Similarity	NPC43945
0.6795	Remote Similarity	NPC98880
0.679	Remote Similarity	NPC189371
0.6782	Remote Similarity	NPC252067
0.6782	Remote Similarity	NPC474354
0.6782	Remote Similarity	NPC475710
0.6778	Remote Similarity	NPC19256
0.6771	Remote Similarity	NPC239854
0.6768	Remote Similarity	NPC21929
0.6768	Remote Similarity	NPC27252
0.6768	Remote Similarity	NPC472979
0.6768	Remote Similarity	NPC472980
0.6757	Remote Similarity	NPC200624
0.675	Remote Similarity	NPC285679
0.6744	Remote Similarity	NPC104070
0.6735	Remote Similarity	NPC117115
0.6709	Remote Similarity	NPC229235
0.6706	Remote Similarity	NPC231986
0.6706	Remote Similarity	NPC145053
0.6705	Remote Similarity	NPC474211
0.6705	Remote Similarity	NPC243166
0.6705	Remote Similarity	NPC93843
0.6702	Remote Similarity	NPC251579
0.6702	Remote Similarity	NPC133135
0.67	Remote Similarity	NPC64642
0.67	Remote Similarity	NPC470252
0.67	Remote Similarity	NPC472982
0.67	Remote Similarity	NPC475006
0.67	Remote Similarity	NPC149455
0.6667	Remote Similarity	NPC82770
0.6667	Remote Similarity	NPC469894
0.6667	Remote Similarity	NPC239931
0.6667	Remote Similarity	NPC122327

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 NPC54269 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	809
0.1-0.2	774
0.2-0.3	2495
0.3-0.4	3148
0.4-0.5	1314
0.5-0.6	442
0.6-0.7	136
0.7-0.8	32
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
0.8261	Intermediate Similarity	NPD675	Discontinued
0.7901	Intermediate Similarity	NPD4544	Approved
0.7848	Intermediate Similarity	NPD3903	Approved
0.7848	Intermediate Similarity	NPD3981	Approved
0.7848	Intermediate Similarity	NPD3979	Approved
0.7848	Intermediate Similarity	NPD3904	Approved
0.7778	Intermediate Similarity	NPD4635	Approved
0.7711	Intermediate Similarity	NPD3099	Discontinued
0.7614	Intermediate Similarity	NPD6049	Phase 2
0.7614	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5288	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3035	Approved
0.747	Intermediate Similarity	NPD3427	Approved
0.747	Intermediate Similarity	NPD3429	Approved
0.7467	Intermediate Similarity	NPD9497	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1673	Approved
0.7444	Intermediate Similarity	NPD3495	Discontinued
0.7439	Intermediate Similarity	NPD4170	Approved
0.7439	Intermediate Similarity	NPD4169	Approved
0.7439	Intermediate Similarity	NPD4701	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3426	Approved
0.7412	Intermediate Similarity	NPD3428	Approved
0.7349	Intermediate Similarity	NPD3971	Phase 1
0.7349	Intermediate Similarity	NPD2001	Discontinued
0.7333	Intermediate Similarity	NPD3093	Approved
0.7303	Intermediate Similarity	NPD3980	Approved
0.7303	Intermediate Similarity	NPD3982	Approved
0.7303	Intermediate Similarity	NPD2878	Approved
0.7294	Intermediate Similarity	NPD4409	Approved
0.7294	Intermediate Similarity	NPD4406	Approved
0.7253	Intermediate Similarity	NPD5597	Approved
0.7253	Intermediate Similarity	NPD5598	Approved
0.725	Intermediate Similarity	NPD4147	Approved
0.725	Intermediate Similarity	NPD4144	Approved
0.7191	Intermediate Similarity	NPD4405	Approved
0.7191	Intermediate Similarity	NPD4408	Approved
0.7191	Intermediate Similarity	NPD4407	Approved
0.7191	Intermediate Similarity	NPD7631	Approved
0.7162	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD3346	Approved
0.7159	Intermediate Similarity	NPD3344	Approved
0.7126	Intermediate Similarity	NPD3345	Approved
0.7111	Intermediate Similarity	NPD4542	Approved
0.7111	Intermediate Similarity	NPD4545	Approved
0.7108	Intermediate Similarity	NPD4026	Approved
0.7108	Intermediate Similarity	NPD4027	Approved
0.7079	Intermediate Similarity	NPD7609	Phase 3
0.7073	Intermediate Similarity	NPD1475	Approved
0.7053	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD292	Approved
0.7051	Intermediate Similarity	NPD294	Approved
0.7021	Intermediate Similarity	NPD6354	Discontinued
0.7011	Intermediate Similarity	NPD2002	Discontinued
0.7011	Intermediate Similarity	NPD4146	Approved
0.7011	Intermediate Similarity	NPD4145	Approved
0.6989	Remote Similarity	NPD5832	Phase 3
0.6988	Remote Similarity	NPD1617	Discontinued
0.6977	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD5916	Discontinued
0.6957	Remote Similarity	NPD2895	Discontinued
0.6941	Remote Similarity	NPD4000	Phase 3
0.6932	Remote Similarity	NPD5675	Discontinued
0.6897	Remote Similarity	NPD4636	Approved
0.6882	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5178	Approved
0.6854	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD650	Approved
0.6818	Remote Similarity	NPD1087	Approved
0.6786	Remote Similarity	NPD260	Discontinued
0.6782	Remote Similarity	NPD2205	Approved
0.6782	Remote Similarity	NPD2208	Approved
0.6778	Remote Similarity	NPD5915	Approved
0.6774	Remote Similarity	NPD6472	Discontinued
0.6747	Remote Similarity	NPD9563	Approved
0.6747	Remote Similarity	NPD79	Approved
0.6747	Remote Similarity	NPD9564	Approved
0.6744	Remote Similarity	NPD1185	Approved
0.6742	Remote Similarity	NPD1101	Approved
0.6702	Remote Similarity	NPD713	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD589	Approved
0.6667	Remote Similarity	NPD9588	Approved
0.6667	Remote Similarity	NPD80	Approved
0.6667	Remote Similarity	NPD9589	Approved
0.6667	Remote Similarity	NPD2538	Approved
0.6667	Remote Similarity	NPD9592	Approved
0.6667	Remote Similarity	NPD9590	Approved
0.6667	Remote Similarity	NPD9591	Approved
0.6667	Remote Similarity	NPD9594	Approved
0.6667	Remote Similarity	NPD590	Approved
0.6667	Remote Similarity	NPD2539	Approved
0.6667	Remote Similarity	NPD9593	Approved
0.6667	Remote Similarity	NPD7170	Discontinued
0.6598	Remote Similarity	NPD4321	Approved
0.6596	Remote Similarity	NPD1989	Approved
0.6596	Remote Similarity	NPD3456	Approved
0.6596	Remote Similarity	NPD3457	Approved
0.6596	Remote Similarity	NPD3458	Approved
0.6596	Remote Similarity	NPD2005	Discontinued
0.6593	Remote Similarity	NPD1086	Approved
0.6593	Remote Similarity	NPD1090	Approved
0.6593	Remote Similarity	NPD1089	Approved
0.6588	Remote Similarity	NPD5371	Approved
0.6588	Remote Similarity	NPD914	Suspended
0.6588	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5372	Approved
0.6562	Remote Similarity	NPD4737	Phase 2
0.6562	Remote Similarity	NPD2066	Phase 3
0.6559	Remote Similarity	NPD1563	Approved
0.6552	Remote Similarity	NPD423	Phase 3
0.6543	Remote Similarity	NPD9728	Phase 1
0.6522	Remote Similarity	NPD4543	Discontinued
0.6517	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD942	Approved
0.6489	Remote Similarity	NPD5554	Approved
0.6489	Remote Similarity	NPD4814	Discontinued
0.6489	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD800	Approved
0.6484	Remote Similarity	NPD771	Phase 3
0.6471	Remote Similarity	NPD1051	Approved
0.6471	Remote Similarity	NPD1052	Approved
0.6471	Remote Similarity	NPD1053	Approved
0.6465	Remote Similarity	NPD4936	Approved
0.6465	Remote Similarity	NPD4937	Approved
0.6463	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4263	Approved
0.6458	Remote Similarity	NPD4813	Approved
0.6452	Remote Similarity	NPD1088	Approved
0.6452	Remote Similarity	NPD1508	Approved
0.6444	Remote Similarity	NPD782	Approved
0.6444	Remote Similarity	NPD781	Approved
0.6444	Remote Similarity	NPD783	Approved
0.6444	Remote Similarity	NPD780	Approved
0.6442	Remote Similarity	NPD7635	Approved
0.6429	Remote Similarity	NPD4734	Approved
0.6429	Remote Similarity	NPD5753	Discontinued
0.6429	Remote Similarity	NPD4735	Approved
0.6429	Remote Similarity	NPD603	Approved
0.6421	Remote Similarity	NPD5963	Phase 2
0.6421	Remote Similarity	NPD5964	Phase 2
0.6413	Remote Similarity	NPD4728	Approved
0.6413	Remote Similarity	NPD3673	Approved
0.6413	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3672	Approved
0.6408	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD845	Approved
0.6383	Remote Similarity	NPD1409	Phase 3
0.6383	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD1566	Phase 3
0.6354	Remote Similarity	NPD1565	Approved
0.6354	Remote Similarity	NPD1564	Approved
0.6353	Remote Similarity	NPD295	Approved
0.6353	Remote Similarity	NPD296	Approved
0.6353	Remote Similarity	NPD293	Approved
0.6344	Remote Similarity	NPD2998	Approved
0.6344	Remote Similarity	NPD1239	Approved
0.6344	Remote Similarity	NPD2997	Approved
0.6344	Remote Similarity	NPD517	Discontinued
0.6344	Remote Similarity	NPD3000	Approved
0.6327	Remote Similarity	NPD5630	Phase 1
0.6316	Remote Similarity	NPD1693	Approved
0.6316	Remote Similarity	NPD4094	Approved
0.6304	Remote Similarity	NPD5347	Phase 2
0.6304	Remote Similarity	NPD5346	Phase 2
0.6275	Remote Similarity	NPD2342	Discontinued
0.6263	Remote Similarity	NPD2841	Approved
0.6262	Remote Similarity	NPD3317	Approved
0.625	Remote Similarity	NPD1738	Approved
0.625	Remote Similarity	NPD1843	Approved
0.625	Remote Similarity	NPD2384	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD4007	Approved
0.6224	Remote Similarity	NPD4008	Approved
0.6224	Remote Similarity	NPD1946	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD3020	Approved
0.6222	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD3719	Approved
0.6211	Remote Similarity	NPD3718	Approved
0.6204	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.62	Remote Similarity	NPD1929	Approved
0.62	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.62	Remote Similarity	NPD1930	Approved
0.619	Remote Similarity	NPD9716	Approved
0.6186	Remote Similarity	NPD4655	Approved
0.6186	Remote Similarity	NPD4657	Approved
0.618	Remote Similarity	NPD263	Approved
0.618	Remote Similarity	NPD830	Approved
0.618	Remote Similarity	NPD831	Approved
0.618	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.618	Remote Similarity	NPD262	Approved
0.6168	Remote Similarity	NPD2508	Discontinued
0.6168	Remote Similarity	NPD5951	Approved
0.6163	Remote Similarity	NPD9393	Approved
0.6163	Remote Similarity	NPD9397	Approved
0.6163	Remote Similarity	NPD227	Approved
0.6163	Remote Similarity	NPD225	Approved
0.6162	Remote Similarity	NPD1916	Discontinued
0.6154	Remote Similarity	NPD1697	Approved
0.6146	Remote Similarity	NPD2656	Approved
0.6146	Remote Similarity	NPD2655	Approved
0.6139	Remote Similarity	NPD3048	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