NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	3.662
LogD:	3.384
LogS:	-4.245
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.762
Synthetic Accessibility Score:	3.922
Fsp3:	0.667
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:	-4.676
MDCK Permeability:	2.492723797331564e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.128
Plasma Protein Binding (PPB):	92.07193756103516%
Volume Distribution (VD):	0.821
Pgp-substrate:	14.51437759399414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.466
CYP2C9-inhibitor:	0.4
CYP2C9-substrate:	0.664
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.517
CYP3A4-inhibitor:	0.052
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	15.944
Half-life (T1/2):	0.299

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.16
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.929
Maximum Recommended Daily Dose:	0.165
Skin Sensitization:	0.298
Carcinogencity:	0.93
Eye Corrosion:	0.199
Eye Irritation:	0.345
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC282293

Natural Product ID:	NPC282293
*Common Name:**	7-Ketoisodrimenin
IUPAC Name:	(5aS,9aS)-6,6,9a-trimethyl-3,5,5a,7,8,9-hexahydrobenzo[g][2]benzofuran-1,4-dione
Synonyms:	7-Ketoisodrimenin
Standard InCHIKey:	DUXBZCLJTPCFOX-NHYWBVRUSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-14(2)5-4-6-15(3)11(14)7-10(16)9-8-18-13(17)12(9)15/h11H,4-8H2,1-3H3/t11-,15-/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1CC(=O)C1=C2C(=O)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451021
PubChem CID:	13281820
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
NPO33499	porella cordeana	Species	Porellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350093]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	1000.0	ug ml-1	PMID[558974]

☑ 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 NPC282293 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	1386
0.2-0.3	6037
0.3-0.4	13261
0.4-0.5	10492
0.5-0.6	6861
0.6-0.7	3762
0.7-0.8	646
0.8-0.85	43
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9467	High Similarity	NPC316500
0.9221	High Similarity	NPC150646
0.9012	High Similarity	NPC189311
0.8765	High Similarity	NPC193198
0.8706	High Similarity	NPC8062
0.8659	High Similarity	NPC30486
0.8659	High Similarity	NPC71626
0.8588	High Similarity	NPC5509
0.8537	High Similarity	NPC22611
0.8506	High Similarity	NPC115021
0.8488	Intermediate Similarity	NPC161638
0.8488	Intermediate Similarity	NPC51486
0.8471	Intermediate Similarity	NPC226863
0.8452	Intermediate Similarity	NPC474062
0.8415	Intermediate Similarity	NPC200513
0.8409	Intermediate Similarity	NPC84893
0.8409	Intermediate Similarity	NPC474555
0.8395	Intermediate Similarity	NPC195424
0.8375	Intermediate Similarity	NPC471220
0.8333	Intermediate Similarity	NPC177932
0.8295	Intermediate Similarity	NPC271652
0.8256	Intermediate Similarity	NPC472302
0.8256	Intermediate Similarity	NPC215831
0.8235	Intermediate Similarity	NPC220478
0.8222	Intermediate Similarity	NPC17578
0.8222	Intermediate Similarity	NPC240673
0.8214	Intermediate Similarity	NPC149869
0.8214	Intermediate Similarity	NPC475100
0.8202	Intermediate Similarity	NPC470697
0.8193	Intermediate Similarity	NPC268122
0.8193	Intermediate Similarity	NPC186276
0.8182	Intermediate Similarity	NPC177037
0.8182	Intermediate Similarity	NPC472814
0.8171	Intermediate Similarity	NPC474956
0.8161	Intermediate Similarity	NPC73995
0.8161	Intermediate Similarity	NPC284561
0.8152	Intermediate Similarity	NPC54705
0.814	Intermediate Similarity	NPC312561
0.8118	Intermediate Similarity	NPC65661
0.8118	Intermediate Similarity	NPC86316
0.8118	Intermediate Similarity	NPC106416
0.8111	Intermediate Similarity	NPC209355
0.8111	Intermediate Similarity	NPC295347
0.8095	Intermediate Similarity	NPC118423
0.809	Intermediate Similarity	NPC475657
0.8072	Intermediate Similarity	NPC475665
0.8068	Intermediate Similarity	NPC152467
0.8068	Intermediate Similarity	NPC220454
0.8068	Intermediate Similarity	NPC212679
0.8068	Intermediate Similarity	NPC469595
0.8025	Intermediate Similarity	NPC189206
0.8025	Intermediate Similarity	NPC472300
0.8022	Intermediate Similarity	NPC476797
0.8	Intermediate Similarity	NPC120158
0.8	Intermediate Similarity	NPC65650
0.8	Intermediate Similarity	NPC474554
0.8	Intermediate Similarity	NPC475193
0.8	Intermediate Similarity	NPC53685
0.7978	Intermediate Similarity	NPC472953
0.7976	Intermediate Similarity	NPC178676
0.7957	Intermediate Similarity	NPC117685
0.7957	Intermediate Similarity	NPC474012
0.7957	Intermediate Similarity	NPC476299
0.7955	Intermediate Similarity	NPC168131
0.7955	Intermediate Similarity	NPC174342
0.7955	Intermediate Similarity	NPC280833
0.7955	Intermediate Similarity	NPC173042
0.7935	Intermediate Similarity	NPC38530
0.7935	Intermediate Similarity	NPC208094
0.7935	Intermediate Similarity	NPC2049
0.7935	Intermediate Similarity	NPC84335
0.7935	Intermediate Similarity	NPC53844
0.7931	Intermediate Similarity	NPC477228
0.7931	Intermediate Similarity	NPC171722
0.7907	Intermediate Similarity	NPC110405
0.7907	Intermediate Similarity	NPC323765
0.7901	Intermediate Similarity	NPC473223
0.7901	Intermediate Similarity	NPC40353
0.7901	Intermediate Similarity	NPC27205
0.7872	Intermediate Similarity	NPC471075
0.7865	Intermediate Similarity	NPC232426
0.7865	Intermediate Similarity	NPC113393
0.7865	Intermediate Similarity	NPC281942
0.7841	Intermediate Similarity	NPC477128
0.7841	Intermediate Similarity	NPC307298
0.7841	Intermediate Similarity	NPC80335
0.7826	Intermediate Similarity	NPC154526
0.7826	Intermediate Similarity	NPC472362
0.7826	Intermediate Similarity	NPC242848
0.7826	Intermediate Similarity	NPC472363
0.7816	Intermediate Similarity	NPC195640
0.7816	Intermediate Similarity	NPC250981
0.7816	Intermediate Similarity	NPC168248
0.7805	Intermediate Similarity	NPC54996
0.7802	Intermediate Similarity	NPC477130
0.7802	Intermediate Similarity	NPC477129
0.7802	Intermediate Similarity	NPC38830
0.7802	Intermediate Similarity	NPC148463
0.7791	Intermediate Similarity	NPC474359
0.7791	Intermediate Similarity	NPC469407
0.7791	Intermediate Similarity	NPC60951
0.7778	Intermediate Similarity	NPC65513
0.7778	Intermediate Similarity	NPC141831
0.7765	Intermediate Similarity	NPC94200
0.7765	Intermediate Similarity	NPC471218
0.7753	Intermediate Similarity	NPC285982
0.7753	Intermediate Similarity	NPC251528
0.7742	Intermediate Similarity	NPC132753
0.7742	Intermediate Similarity	NPC175351
0.7742	Intermediate Similarity	NPC475709
0.7742	Intermediate Similarity	NPC151681
0.7742	Intermediate Similarity	NPC121402
0.7742	Intermediate Similarity	NPC224356
0.7738	Intermediate Similarity	NPC268827
0.7717	Intermediate Similarity	NPC183012
0.7711	Intermediate Similarity	NPC184737
0.7711	Intermediate Similarity	NPC35574
0.7708	Intermediate Similarity	NPC159533
0.7701	Intermediate Similarity	NPC472442
0.7701	Intermediate Similarity	NPC476678
0.7692	Intermediate Similarity	NPC166346
0.7692	Intermediate Similarity	NPC476597
0.7692	Intermediate Similarity	NPC472303
0.7692	Intermediate Similarity	NPC476598
0.7692	Intermediate Similarity	NPC139692
0.7684	Intermediate Similarity	NPC476888
0.7684	Intermediate Similarity	NPC93744
0.7683	Intermediate Similarity	NPC41017
0.7674	Intermediate Similarity	NPC271784
0.7674	Intermediate Similarity	NPC477124
0.7674	Intermediate Similarity	NPC472440
0.7674	Intermediate Similarity	NPC470047
0.7674	Intermediate Similarity	NPC470046
0.7667	Intermediate Similarity	NPC477782
0.7667	Intermediate Similarity	NPC101651
0.7667	Intermediate Similarity	NPC471818
0.7667	Intermediate Similarity	NPC159748
0.7667	Intermediate Similarity	NPC469372
0.7667	Intermediate Similarity	NPC472307
0.766	Intermediate Similarity	NPC316598
0.7654	Intermediate Similarity	NPC20025
0.7647	Intermediate Similarity	NPC474955
0.7647	Intermediate Similarity	NPC40228
0.7647	Intermediate Similarity	NPC14203
0.7647	Intermediate Similarity	NPC229584
0.764	Intermediate Similarity	NPC196407
0.764	Intermediate Similarity	NPC24816
0.7634	Intermediate Similarity	NPC112654
0.7634	Intermediate Similarity	NPC29952
0.7619	Intermediate Similarity	NPC254996
0.7619	Intermediate Similarity	NPC268502
0.7619	Intermediate Similarity	NPC471299
0.7614	Intermediate Similarity	NPC470051
0.7614	Intermediate Similarity	NPC470050
0.7614	Intermediate Similarity	NPC475181
0.7614	Intermediate Similarity	NPC229717
0.7614	Intermediate Similarity	NPC194417
0.7614	Intermediate Similarity	NPC471219
0.7609	Intermediate Similarity	NPC476415
0.7609	Intermediate Similarity	NPC476596
0.7609	Intermediate Similarity	NPC184870
0.7604	Intermediate Similarity	NPC40918
0.7604	Intermediate Similarity	NPC476890
0.7604	Intermediate Similarity	NPC80781
0.759	Intermediate Similarity	NPC97377
0.759	Intermediate Similarity	NPC187568
0.759	Intermediate Similarity	NPC41780
0.7586	Intermediate Similarity	NPC109512
0.7586	Intermediate Similarity	NPC32223
0.7582	Intermediate Similarity	NPC303697
0.7582	Intermediate Similarity	NPC49420
0.7582	Intermediate Similarity	NPC477783
0.7582	Intermediate Similarity	NPC190442
0.7582	Intermediate Similarity	NPC473944
0.7582	Intermediate Similarity	NPC186363
0.7582	Intermediate Similarity	NPC252433
0.7582	Intermediate Similarity	NPC233345
0.7582	Intermediate Similarity	NPC289479
0.7579	Intermediate Similarity	NPC472644
0.7579	Intermediate Similarity	NPC476933
0.7579	Intermediate Similarity	NPC110897
0.7558	Intermediate Similarity	NPC321289
0.7558	Intermediate Similarity	NPC100297
0.7558	Intermediate Similarity	NPC226988
0.7558	Intermediate Similarity	NPC327969
0.7556	Intermediate Similarity	NPC177141
0.7556	Intermediate Similarity	NPC474570
0.7553	Intermediate Similarity	NPC478233
0.7553	Intermediate Similarity	NPC476768
0.7553	Intermediate Similarity	NPC476253
0.7553	Intermediate Similarity	NPC110937
0.7529	Intermediate Similarity	NPC47747
0.7528	Intermediate Similarity	NPC38885
0.7528	Intermediate Similarity	NPC181327
0.7527	Intermediate Similarity	NPC473369
0.7527	Intermediate Similarity	NPC33473
0.7526	Intermediate Similarity	NPC475526
0.7526	Intermediate Similarity	NPC329345
0.7526	Intermediate Similarity	NPC476770
0.7526	Intermediate Similarity	NPC470954

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 NPC282293 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1897
0.2-0.3	3969
0.3-0.4	2063
0.4-0.5	652
0.5-0.6	261
0.6-0.7	112
0.7-0.8	11
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8415	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1694	Approved
0.7816	Intermediate Similarity	NPD7334	Approved
0.7816	Intermediate Similarity	NPD7521	Approved
0.7816	Intermediate Similarity	NPD7146	Approved
0.7816	Intermediate Similarity	NPD5330	Approved
0.7816	Intermediate Similarity	NPD6409	Approved
0.7816	Intermediate Similarity	NPD6684	Approved
0.764	Intermediate Similarity	NPD6903	Approved
0.764	Intermediate Similarity	NPD5737	Approved
0.764	Intermediate Similarity	NPD6672	Approved
0.764	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5693	Phase 1
0.7253	Intermediate Similarity	NPD5208	Approved
0.7174	Intermediate Similarity	NPD6673	Approved
0.7174	Intermediate Similarity	NPD6904	Approved
0.7174	Intermediate Similarity	NPD6080	Approved
0.7158	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD8039	Approved
0.7143	Intermediate Similarity	NPD3573	Approved
0.7129	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5207	Approved
0.7097	Intermediate Similarity	NPD5692	Phase 3
0.7093	Intermediate Similarity	NPD3617	Approved
0.7053	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7748	Approved
0.7053	Intermediate Similarity	NPD7900	Approved
0.7033	Intermediate Similarity	NPD6098	Approved
0.7021	Intermediate Similarity	NPD6050	Approved
0.7021	Intermediate Similarity	NPD5694	Approved
0.701	Intermediate Similarity	NPD6084	Phase 2
0.701	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD3666	Approved
0.7	Intermediate Similarity	NPD3133	Approved
0.699	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5209	Approved
0.6947	Remote Similarity	NPD6399	Phase 3
0.6939	Remote Similarity	NPD5696	Approved
0.6939	Remote Similarity	NPD7638	Approved
0.6939	Remote Similarity	NPD4225	Approved
0.6923	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6001	Approved
0.6869	Remote Similarity	NPD7639	Approved
0.6869	Remote Similarity	NPD7640	Approved
0.6852	Remote Similarity	NPD7115	Discovery
0.6848	Remote Similarity	NPD4623	Approved
0.6848	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4519	Discontinued
0.6848	Remote Similarity	NPD3618	Phase 1
0.6842	Remote Similarity	NPD7515	Phase 2
0.6837	Remote Similarity	NPD7902	Approved
0.6809	Remote Similarity	NPD6051	Approved
0.6804	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5654	Approved
0.6778	Remote Similarity	NPD4223	Phase 3
0.6778	Remote Similarity	NPD4221	Approved
0.6778	Remote Similarity	NPD3667	Approved
0.6747	Remote Similarity	NPD4137	Phase 3
0.6737	Remote Similarity	NPD5785	Approved
0.6733	Remote Similarity	NPD7632	Discontinued
0.6731	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD4691	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6632	Remote Similarity	NPD4753	Phase 2
0.6632	Remote Similarity	NPD5328	Approved
0.6632	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4786	Approved
0.663	Remote Similarity	NPD4197	Approved
0.663	Remote Similarity	NPD3668	Phase 3
0.6588	Remote Similarity	NPD5777	Approved
0.6566	Remote Similarity	NPD7732	Phase 3
0.6559	Remote Similarity	NPD5329	Approved
0.6556	Remote Similarity	NPD4695	Discontinued
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD6008	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6495	Remote Similarity	NPD6079	Approved
0.6495	Remote Similarity	NPD6411	Approved
0.6489	Remote Similarity	NPD4689	Approved
0.6489	Remote Similarity	NPD5690	Phase 2
0.6489	Remote Similarity	NPD5280	Approved
0.6489	Remote Similarity	NPD4690	Approved
0.6489	Remote Similarity	NPD4138	Approved
0.6489	Remote Similarity	NPD4693	Phase 3
0.6489	Remote Similarity	NPD4694	Approved
0.6489	Remote Similarity	NPD4688	Approved
0.6489	Remote Similarity	NPD5205	Approved
0.6484	Remote Similarity	NPD4139	Approved
0.6484	Remote Similarity	NPD4692	Approved
0.6476	Remote Similarity	NPD5697	Approved
0.6476	Remote Similarity	NPD5701	Approved
0.6437	Remote Similarity	NPD4058	Approved
0.6437	Remote Similarity	NPD4687	Approved
0.6437	Remote Similarity	NPD5733	Approved
0.6429	Remote Similarity	NPD5779	Approved
0.6429	Remote Similarity	NPD4202	Approved
0.6429	Remote Similarity	NPD5778	Approved
0.6415	Remote Similarity	NPD6899	Approved
0.6415	Remote Similarity	NPD6011	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD6881	Approved
0.6395	Remote Similarity	NPD5276	Approved
0.6355	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD6013	Approved
0.6355	Remote Similarity	NPD6014	Approved
0.6355	Remote Similarity	NPD6012	Approved
0.6355	Remote Similarity	NPD6373	Approved
0.6346	Remote Similarity	NPD6052	Approved
0.63	Remote Similarity	NPD4629	Approved
0.63	Remote Similarity	NPD5210	Approved
0.6296	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD6883	Approved
0.6296	Remote Similarity	NPD7102	Approved
0.6289	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6101	Approved
0.6277	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD7341	Phase 2
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.6239	Remote Similarity	NPD6869	Approved
0.6238	Remote Similarity	NPD5222	Approved
0.6238	Remote Similarity	NPD7614	Phase 1
0.6238	Remote Similarity	NPD4697	Phase 3
0.6238	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5221	Approved
0.6235	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6404	Discontinued
0.6211	Remote Similarity	NPD5363	Approved
0.6211	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD1696	Phase 3
0.619	Remote Similarity	NPD4224	Phase 2
0.6182	Remote Similarity	NPD6053	Discontinued
0.6182	Remote Similarity	NPD8297	Approved
0.6182	Remote Similarity	NPD6882	Approved
0.618	Remote Similarity	NPD3702	Approved
0.6176	Remote Similarity	NPD4755	Approved
0.6176	Remote Similarity	NPD5173	Approved
0.617	Remote Similarity	NPD4788	Approved
0.6168	Remote Similarity	NPD6412	Phase 2
0.6168	Remote Similarity	NPD6614	Approved
0.6162	Remote Similarity	NPD7637	Suspended
0.6162	Remote Similarity	NPD8035	Phase 2
0.6162	Remote Similarity	NPD8034	Phase 2
0.6154	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6371	Approved
0.6145	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7094	Approved
0.6126	Remote Similarity	NPD6858	Approved
0.6125	Remote Similarity	NPD287	Approved
0.6122	Remote Similarity	NPD1695	Approved
0.61	Remote Similarity	NPD5133	Approved
0.6095	Remote Similarity	NPD5211	Phase 2
0.6087	Remote Similarity	NPD6319	Approved
0.6087	Remote Similarity	NPD4195	Approved
0.6083	Remote Similarity	NPD7319	Approved
0.6071	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD4270	Approved
0.6064	Remote Similarity	NPD4269	Approved
0.6061	Remote Similarity	NPD46	Approved
0.6061	Remote Similarity	NPD4096	Approved
0.6061	Remote Similarity	NPD6698	Approved
0.6058	Remote Similarity	NPD5286	Approved
0.6058	Remote Similarity	NPD4700	Approved
0.6058	Remote Similarity	NPD5285	Approved
0.6058	Remote Similarity	NPD4696	Approved
0.6042	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5282	Discontinued
0.6018	Remote Similarity	NPD6274	Approved
0.6018	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD5223	Approved
0.5983	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD4632	Approved
0.5981	Remote Similarity	NPD5141	Approved
0.5979	Remote Similarity	NPD5786	Approved
0.5966	Remote Similarity	NPD7507	Approved
0.5965	Remote Similarity	NPD6317	Approved
0.5963	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5369	Approved
0.5943	Remote Similarity	NPD4633	Approved
0.5943	Remote Similarity	NPD5224	Approved
0.5943	Remote Similarity	NPD5225	Approved
0.5943	Remote Similarity	NPD5226	Approved
0.5922	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6314	Approved
0.5913	Remote Similarity	NPD6313	Approved
0.5913	Remote Similarity	NPD6335	Approved
0.5909	Remote Similarity	NPD8132	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data