NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.15
Volume:	237.338
LogP:	3.492
LogD:	3.437
LogS:	-3.793
# Rotatable Bonds:	0
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.463
Synthetic Accessibility Score:	4.374
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.573
MDCK Permeability:	2.696878982533235e-05
Pgp-inhibitor:	0.9
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.961
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.857
Plasma Protein Binding (PPB):	83.84966278076172%
Volume Distribution (VD):	1.172
Pgp-substrate:	16.073638916015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.255
CYP2C19-inhibitor:	0.805
CYP2C19-substrate:	0.541
CYP2C9-inhibitor:	0.225
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.479
CYP3A4-inhibitor:	0.836
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	13.645
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.262
AMES Toxicity:	0.21
Rat Oral Acute Toxicity:	0.208
Maximum Recommended Daily Dose:	0.379
Skin Sensitization:	0.949
Carcinogencity:	0.427
Eye Corrosion:	0.934
Eye Irritation:	0.981
Respiratory Toxicity:	0.869

Download Data

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

Natural Product: NPC41017

Natural Product ID:	NPC41017
*Common Name:**	Oblongolide
IUPAC Name:	(3aS,5aR,7S,9aS,9bR)-7,9b-dimethyl-3,3a,5a,6,7,8,9,9a-octahydrobenzo[g][2]benzofuran-1-one
Synonyms:	Oblongolide
Standard InCHIKey:	ZSRQNNNSHRCNQE-HNRZYHPDSA-N
Standard InCHI:	InChI=1S/C14H20O2/c1-9-3-6-12-10(7-9)4-5-11-8-16-13(15)14(11,12)2/h4-5,9-12H,3,6-8H2,1-2H3/t9-,10-,11+,12-,14-/m0/s1
SMILES:	C[C@H]1CC[C@H]2[C@@H](C=C[C@@H]3COC(=O)[C@]23C)C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077021
PubChem CID:	176630
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO33230	Phomopsis sp. BCC 9789	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038128]

☑ 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	4
MIC	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	227000.0	nM	PMID[493069]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	91000.0	nM	PMID[493069]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	91000.0	nM	PMID[493069]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	227000.0	nM	PMID[493069]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	>	227000.0	nM	PMID[493069]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	91000.0	nM	PMID[493069]

☑ 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 NPC41017 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	160
0.1-0.2	1072
0.2-0.3	6187
0.3-0.4	15860
0.4-0.5	7333
0.5-0.6	7079
0.6-0.7	4252
0.7-0.8	700
0.8-0.85	45
0.85-0.9	6
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC195424
0.9189	High Similarity	NPC35574
0.8846	High Similarity	NPC22611
0.8611	High Similarity	NPC199557
0.8608	High Similarity	NPC470948
0.859	High Similarity	NPC475665
0.8537	High Similarity	NPC215831
0.8537	High Similarity	NPC477128
0.8519	High Similarity	NPC6979
0.85	High Similarity	NPC139566
0.85	High Similarity	NPC100391
0.8481	Intermediate Similarity	NPC186276
0.8481	Intermediate Similarity	NPC178676
0.8442	Intermediate Similarity	NPC4827
0.8434	Intermediate Similarity	NPC73995
0.84	Intermediate Similarity	NPC166797
0.8395	Intermediate Similarity	NPC470223
0.8354	Intermediate Similarity	NPC474955
0.8333	Intermediate Similarity	NPC15059
0.8333	Intermediate Similarity	NPC327674
0.8293	Intermediate Similarity	NPC264127
0.8272	Intermediate Similarity	NPC469569
0.8214	Intermediate Similarity	NPC168131
0.8193	Intermediate Similarity	NPC167877
0.8182	Intermediate Similarity	NPC899
0.8182	Intermediate Similarity	NPC92489
0.8182	Intermediate Similarity	NPC69143
0.8171	Intermediate Similarity	NPC110405
0.8171	Intermediate Similarity	NPC52628
0.8158	Intermediate Similarity	NPC306928
0.8125	Intermediate Similarity	NPC38642
0.8125	Intermediate Similarity	NPC327002
0.8118	Intermediate Similarity	NPC469595
0.8118	Intermediate Similarity	NPC220454
0.8118	Intermediate Similarity	NPC212679
0.8118	Intermediate Similarity	NPC152467
0.8095	Intermediate Similarity	NPC226863
0.8095	Intermediate Similarity	NPC97884
0.8095	Intermediate Similarity	NPC472220
0.8095	Intermediate Similarity	NPC474845
0.8095	Intermediate Similarity	NPC28227
0.8077	Intermediate Similarity	NPC316500
0.8077	Intermediate Similarity	NPC472300
0.8052	Intermediate Similarity	NPC279666
0.8052	Intermediate Similarity	NPC192540
0.8049	Intermediate Similarity	NPC312660
0.8046	Intermediate Similarity	NPC477130
0.8046	Intermediate Similarity	NPC477129
0.8025	Intermediate Similarity	NPC240302
0.8023	Intermediate Similarity	NPC65513
0.8023	Intermediate Similarity	NPC49420
0.8023	Intermediate Similarity	NPC233345
0.8023	Intermediate Similarity	NPC186363
0.8	Intermediate Similarity	NPC471222
0.7975	Intermediate Similarity	NPC321514
0.7952	Intermediate Similarity	NPC329738
0.7952	Intermediate Similarity	NPC189311
0.7952	Intermediate Similarity	NPC323765
0.7952	Intermediate Similarity	NPC177932
0.7949	Intermediate Similarity	NPC476601
0.7931	Intermediate Similarity	NPC166346
0.7931	Intermediate Similarity	NPC475657
0.7927	Intermediate Similarity	NPC193198
0.7922	Intermediate Similarity	NPC241854
0.7922	Intermediate Similarity	NPC251970
0.7922	Intermediate Similarity	NPC183503
0.7922	Intermediate Similarity	NPC161923
0.7922	Intermediate Similarity	NPC283908
0.7922	Intermediate Similarity	NPC476046
0.7922	Intermediate Similarity	NPC103958
0.7907	Intermediate Similarity	NPC469372
0.7901	Intermediate Similarity	NPC473420
0.7901	Intermediate Similarity	NPC149237
0.7901	Intermediate Similarity	NPC209318
0.7901	Intermediate Similarity	NPC475951
0.7901	Intermediate Similarity	NPC223330
0.7895	Intermediate Similarity	NPC160817
0.7887	Intermediate Similarity	NPC306750
0.7857	Intermediate Similarity	NPC195640
0.7841	Intermediate Similarity	NPC250075
0.7841	Intermediate Similarity	NPC56525
0.7838	Intermediate Similarity	NPC469868
0.7821	Intermediate Similarity	NPC201027
0.7821	Intermediate Similarity	NPC476795
0.7816	Intermediate Similarity	NPC252433
0.7805	Intermediate Similarity	NPC142683
0.7805	Intermediate Similarity	NPC200513
0.7805	Intermediate Similarity	NPC100297
0.7805	Intermediate Similarity	NPC226988
0.7805	Intermediate Similarity	NPC73882
0.7791	Intermediate Similarity	NPC284561
0.7778	Intermediate Similarity	NPC267517
0.7778	Intermediate Similarity	NPC104545
0.7778	Intermediate Similarity	NPC474956
0.7778	Intermediate Similarity	NPC170038
0.7765	Intermediate Similarity	NPC230016
0.7763	Intermediate Similarity	NPC472955
0.7753	Intermediate Similarity	NPC183012
0.775	Intermediate Similarity	NPC179028
0.7738	Intermediate Similarity	NPC476602
0.7738	Intermediate Similarity	NPC76333
0.7738	Intermediate Similarity	NPC2709
0.7727	Intermediate Similarity	NPC49776
0.7727	Intermediate Similarity	NPC474436
0.7727	Intermediate Similarity	NPC277721
0.7727	Intermediate Similarity	NPC63118
0.7727	Intermediate Similarity	NPC470224
0.7727	Intermediate Similarity	NPC267266
0.7727	Intermediate Similarity	NPC470656
0.7722	Intermediate Similarity	NPC309399
0.7711	Intermediate Similarity	NPC477852
0.7701	Intermediate Similarity	NPC158488
0.7701	Intermediate Similarity	NPC76286
0.7701	Intermediate Similarity	NPC214844
0.7692	Intermediate Similarity	NPC301065
0.7692	Intermediate Similarity	NPC237591
0.7692	Intermediate Similarity	NPC3753
0.7683	Intermediate Similarity	NPC282293
0.7683	Intermediate Similarity	NPC14203
0.7683	Intermediate Similarity	NPC229584
0.7674	Intermediate Similarity	NPC277771
0.7667	Intermediate Similarity	NPC112654
0.7667	Intermediate Similarity	NPC322063
0.7654	Intermediate Similarity	NPC44083
0.7654	Intermediate Similarity	NPC477371
0.7654	Intermediate Similarity	NPC199595
0.7654	Intermediate Similarity	NPC153987
0.7654	Intermediate Similarity	NPC118987
0.7647	Intermediate Similarity	NPC244174
0.7647	Intermediate Similarity	NPC10005
0.7647	Intermediate Similarity	NPC82979
0.7647	Intermediate Similarity	NPC325594
0.7647	Intermediate Similarity	NPC220478
0.7647	Intermediate Similarity	NPC250981
0.7647	Intermediate Similarity	NPC155011
0.7647	Intermediate Similarity	NPC329943
0.7647	Intermediate Similarity	NPC91525
0.7647	Intermediate Similarity	NPC9892
0.7632	Intermediate Similarity	NPC144511
0.7632	Intermediate Similarity	NPC296522
0.7625	Intermediate Similarity	NPC107039
0.7625	Intermediate Similarity	NPC471899
0.7625	Intermediate Similarity	NPC471897
0.7625	Intermediate Similarity	NPC187568
0.7625	Intermediate Similarity	NPC41780
0.7619	Intermediate Similarity	NPC97505
0.7619	Intermediate Similarity	NPC165064
0.7619	Intermediate Similarity	NPC30486
0.7619	Intermediate Similarity	NPC469407
0.7614	Intermediate Similarity	NPC26888
0.7614	Intermediate Similarity	NPC218301
0.7595	Intermediate Similarity	NPC476844
0.759	Intermediate Similarity	NPC15910
0.759	Intermediate Similarity	NPC268122
0.759	Intermediate Similarity	NPC321289
0.759	Intermediate Similarity	NPC327969
0.759	Intermediate Similarity	NPC133391
0.759	Intermediate Similarity	NPC260956
0.7586	Intermediate Similarity	NPC474570
0.7586	Intermediate Similarity	NPC173042
0.7586	Intermediate Similarity	NPC474700
0.7586	Intermediate Similarity	NPC5509
0.7582	Intermediate Similarity	NPC292133
0.7582	Intermediate Similarity	NPC204054
0.7582	Intermediate Similarity	NPC10057
0.7582	Intermediate Similarity	NPC257726
0.7564	Intermediate Similarity	NPC35656
0.7564	Intermediate Similarity	NPC472956
0.7564	Intermediate Similarity	NPC470237
0.7564	Intermediate Similarity	NPC279241
0.7561	Intermediate Similarity	NPC477057
0.7561	Intermediate Similarity	NPC473685
0.7558	Intermediate Similarity	NPC171722
0.7558	Intermediate Similarity	NPC312561
0.7558	Intermediate Similarity	NPC162107
0.7558	Intermediate Similarity	NPC38885
0.7558	Intermediate Similarity	NPC128644
0.7558	Intermediate Similarity	NPC181327
0.7558	Intermediate Similarity	NPC46912
0.7556	Intermediate Similarity	NPC295347
0.7556	Intermediate Similarity	NPC469599
0.7531	Intermediate Similarity	NPC280654
0.7531	Intermediate Similarity	NPC260385
0.7531	Intermediate Similarity	NPC59436
0.7531	Intermediate Similarity	NPC110094
0.7531	Intermediate Similarity	NPC239098
0.7529	Intermediate Similarity	NPC147921
0.7529	Intermediate Similarity	NPC300985
0.7529	Intermediate Similarity	NPC65661
0.7529	Intermediate Similarity	NPC86316
0.7529	Intermediate Similarity	NPC106416
0.7529	Intermediate Similarity	NPC283733
0.7528	Intermediate Similarity	NPC474185
0.7528	Intermediate Similarity	NPC79117
0.75	Intermediate Similarity	NPC474842
0.75	Intermediate Similarity	NPC175628
0.75	Intermediate Similarity	NPC111585
0.75	Intermediate Similarity	NPC124703
0.75	Intermediate Similarity	NPC474728
0.75	Intermediate Similarity	NPC312480

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 NPC41017 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1438
0.2-0.3	4231
0.3-0.4	2269
0.4-0.5	573
0.5-0.6	285
0.6-0.7	172
0.7-0.8	32
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7952	Intermediate Similarity	NPD1694	Approved
0.7857	Intermediate Similarity	NPD6684	Approved
0.7857	Intermediate Similarity	NPD6409	Approved
0.7857	Intermediate Similarity	NPD5330	Approved
0.7857	Intermediate Similarity	NPD7146	Approved
0.7857	Intermediate Similarity	NPD7521	Approved
0.7857	Intermediate Similarity	NPD7334	Approved
0.7805	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6399	Phase 3
0.7701	Intermediate Similarity	NPD5207	Approved
0.7674	Intermediate Similarity	NPD6672	Approved
0.7674	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5737	Approved
0.7674	Intermediate Similarity	NPD6903	Approved
0.7442	Intermediate Similarity	NPD6098	Approved
0.7381	Intermediate Similarity	NPD3667	Approved
0.7375	Intermediate Similarity	NPD8039	Approved
0.7363	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD5208	Approved
0.7253	Intermediate Similarity	NPD6001	Approved
0.7253	Intermediate Similarity	NPD7900	Approved
0.7253	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5694	Approved
0.7209	Intermediate Similarity	NPD4786	Approved
0.7209	Intermediate Similarity	NPD3668	Phase 3
0.7191	Intermediate Similarity	NPD6080	Approved
0.7191	Intermediate Similarity	NPD6673	Approved
0.7191	Intermediate Similarity	NPD6904	Approved
0.7174	Intermediate Similarity	NPD5695	Phase 3
0.7128	Intermediate Similarity	NPD5696	Approved
0.7111	Intermediate Similarity	NPD5692	Phase 3
0.7097	Intermediate Similarity	NPD5349	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7748	Approved
0.7045	Intermediate Similarity	NPD3618	Phase 1
0.7041	Intermediate Similarity	NPD6008	Approved
0.7033	Intermediate Similarity	NPD6050	Approved
0.7033	Intermediate Similarity	NPD5281	Approved
0.7033	Intermediate Similarity	NPD6411	Approved
0.7033	Intermediate Similarity	NPD5284	Approved
0.7033	Intermediate Similarity	NPD5693	Phase 1
0.7021	Intermediate Similarity	NPD7902	Approved
0.7021	Intermediate Similarity	NPD6083	Phase 2
0.7021	Intermediate Similarity	NPD6084	Phase 2
0.7011	Intermediate Similarity	NPD3666	Approved
0.7011	Intermediate Similarity	NPD3133	Approved
0.7011	Intermediate Similarity	NPD3665	Phase 1
0.6848	Remote Similarity	NPD7515	Phase 2
0.6813	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6101	Approved
0.6782	Remote Similarity	NPD4221	Approved
0.6782	Remote Similarity	NPD4223	Phase 3
0.675	Remote Similarity	NPD4137	Phase 3
0.6744	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD4691	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6634	Remote Similarity	NPD5697	Approved
0.6632	Remote Similarity	NPD5654	Approved
0.6632	Remote Similarity	NPD4629	Approved
0.6632	Remote Similarity	NPD5210	Approved
0.6632	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6051	Approved
0.663	Remote Similarity	NPD4753	Phase 2
0.663	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5328	Approved
0.6629	Remote Similarity	NPD4197	Approved
0.6627	Remote Similarity	NPD4058	Approved
0.6627	Remote Similarity	NPD4687	Approved
0.6625	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4225	Approved
0.6596	Remote Similarity	NPD5779	Approved
0.6596	Remote Similarity	NPD5778	Approved
0.6585	Remote Similarity	NPD5777	Approved
0.6569	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD6899	Approved
0.6569	Remote Similarity	NPD6011	Approved
0.6556	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5329	Approved
0.6538	Remote Similarity	NPD6650	Approved
0.6538	Remote Similarity	NPD6649	Approved
0.6535	Remote Similarity	NPD7128	Approved
0.6535	Remote Similarity	NPD6675	Approved
0.6535	Remote Similarity	NPD6402	Approved
0.6535	Remote Similarity	NPD5739	Approved
0.6512	Remote Similarity	NPD3617	Approved
0.6512	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6014	Approved
0.6505	Remote Similarity	NPD6372	Approved
0.6505	Remote Similarity	NPD6012	Approved
0.6505	Remote Similarity	NPD6013	Approved
0.6505	Remote Similarity	NPD6373	Approved
0.6495	Remote Similarity	NPD5959	Approved
0.6484	Remote Similarity	NPD5280	Approved
0.6484	Remote Similarity	NPD4138	Approved
0.6484	Remote Similarity	NPD4694	Approved
0.6484	Remote Similarity	NPD4690	Approved
0.6484	Remote Similarity	NPD5205	Approved
0.6484	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4693	Phase 3
0.6484	Remote Similarity	NPD4688	Approved
0.6484	Remote Similarity	NPD4689	Approved
0.6471	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD6614	Approved
0.6471	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1695	Approved
0.6442	Remote Similarity	NPD6883	Approved
0.6442	Remote Similarity	NPD7290	Approved
0.6442	Remote Similarity	NPD7102	Approved
0.6429	Remote Similarity	NPD7638	Approved
0.6429	Remote Similarity	NPD5733	Approved
0.6421	Remote Similarity	NPD4202	Approved
0.6408	Remote Similarity	NPD7320	Approved
0.6404	Remote Similarity	NPD4269	Approved
0.6404	Remote Similarity	NPD4270	Approved
0.6404	Remote Similarity	NPD6435	Approved
0.6392	Remote Similarity	NPD4697	Phase 3
0.6392	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5222	Approved
0.6392	Remote Similarity	NPD5221	Approved
0.6392	Remote Similarity	NPD7732	Phase 3
0.6389	Remote Similarity	NPD7115	Discovery
0.6386	Remote Similarity	NPD5276	Approved
0.6383	Remote Similarity	NPD5785	Approved
0.6381	Remote Similarity	NPD6847	Approved
0.6381	Remote Similarity	NPD6617	Approved
0.6381	Remote Similarity	NPD6869	Approved
0.6381	Remote Similarity	NPD8130	Phase 1
0.6374	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6354	Remote Similarity	NPD5282	Discontinued
0.6353	Remote Similarity	NPD6942	Approved
0.6353	Remote Similarity	NPD7339	Approved
0.6353	Remote Similarity	NPD3702	Approved
0.6333	Remote Similarity	NPD5362	Discontinued
0.6333	Remote Similarity	NPD7154	Phase 3
0.6329	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5173	Approved
0.6321	Remote Similarity	NPD6882	Approved
0.6321	Remote Similarity	NPD8297	Approved
0.6316	Remote Similarity	NPD7637	Suspended
0.6304	Remote Similarity	NPD5786	Approved
0.6292	Remote Similarity	NPD4139	Approved
0.6292	Remote Similarity	NPD4692	Approved
0.6262	Remote Similarity	NPD6858	Approved
0.6262	Remote Similarity	NPD7094	Approved
0.625	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD28	Approved
0.625	Remote Similarity	NPD29	Approved
0.6235	Remote Similarity	NPD4784	Approved
0.6235	Remote Similarity	NPD4785	Approved
0.6226	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5285	Approved
0.62	Remote Similarity	NPD4696	Approved
0.62	Remote Similarity	NPD5286	Approved
0.62	Remote Similarity	NPD6404	Discontinued
0.6196	Remote Similarity	NPD5363	Approved
0.618	Remote Similarity	NPD4252	Approved
0.618	Remote Similarity	NPD5368	Approved
0.618	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4224	Phase 2
0.617	Remote Similarity	NPD4518	Approved
0.6162	Remote Similarity	NPD4755	Approved
0.6161	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4788	Approved
0.6154	Remote Similarity	NPD6412	Phase 2
0.6154	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6868	Approved
0.6139	Remote Similarity	NPD5223	Approved
0.6129	Remote Similarity	NPD6422	Discontinued
0.6111	Remote Similarity	NPD857	Phase 3
0.6111	Remote Similarity	NPD4632	Approved
0.6104	Remote Similarity	NPD287	Approved
0.6095	Remote Similarity	NPD6686	Approved
0.6091	Remote Similarity	NPD6317	Approved
0.6081	Remote Similarity	NPD3172	Approved
0.6078	Remote Similarity	NPD5211	Phase 2
0.6078	Remote Similarity	NPD4633	Approved
0.6078	Remote Similarity	NPD5225	Approved
0.6078	Remote Similarity	NPD5226	Approved
0.6078	Remote Similarity	NPD5224	Approved
0.6067	Remote Similarity	NPD7645	Phase 2
0.6061	Remote Similarity	NPD7614	Phase 1
0.6061	Remote Similarity	NPD1989	Approved
0.6049	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD6926	Approved
0.6047	Remote Similarity	NPD6924	Approved
0.6047	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD5209	Approved
0.6042	Remote Similarity	NPD3672	Approved
0.6042	Remote Similarity	NPD4096	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