NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	0.713
LogD:	0.579
LogS:	-3.618
# Rotatable Bonds:	2
TPSA:	70.06
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.576
Synthetic Accessibility Score:	5.082
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.845
MDCK Permeability:	2.2799704311182722e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.854
Plasma Protein Binding (PPB):	43.874881744384766%
Volume Distribution (VD):	0.705
Pgp-substrate:	59.25093460083008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.852
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.597

ADMET: Excretion

Clearance (CL):	1.521
Half-life (T1/2):	0.92

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.423
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.959
Rat Oral Acute Toxicity:	0.657
Maximum Recommended Daily Dose:	0.632
Skin Sensitization:	0.931
Carcinogencity:	0.146
Eye Corrosion:	0.051
Eye Irritation:	0.804
Respiratory Toxicity:	0.716

Download Data

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

Natural Product: NPC112613

Natural Product ID:	NPC112613
*Common Name:**	(+)-Phomenone
IUPAC Name:	(1aR,6R,7R,7aR,7bR)-6-hydroxy-1a-(3-hydroxyprop-1-en-2-yl)-7,7a-dimethyl-5,6,7,7b-tetrahydro-4H-naphtho[1,2-b]oxiren-2-one
Synonyms:	(+)-Phomenone
Standard InCHIKey:	WKZMDQXEUJZALS-OANMRLRGSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8(7-16)15-12(18)6-10-4-5-11(17)9(2)14(10,3)13(15)19-15/h6,9,11,13,16-17H,1,4-5,7H2,2-3H3/t9-,11+,13+,14+,15-/m0/s1
SMILES:	C=C(CO)[C@]12C(=O)C=C3CC[C@H]([C@H](C)[C@@]3(C)[C@H]1O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172874
PubChem CID:	93306
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33525	Xylaria sp. BCC 1067	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO32481	Penicillium copticola	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25734623]

☑ 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
EC50	1
IC50	3

Activity Type	# Activity
Cell Line	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	31820.0	nM	PMID[448565]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	6050.0	nM	PMID[448565]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	=	0.32	ug.mL-1	PMID[448564]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	5410.0	nM	PMID[448565]

☑ 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 NPC112613 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	214
0.1-0.2	1323
0.2-0.3	4531
0.3-0.4	7844
0.4-0.5	14545
0.5-0.6	7695
0.6-0.7	5531
0.7-0.8	988
0.8-0.85	13
0.85-0.9	8
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC207885
0.957	High Similarity	NPC94337
0.9263	High Similarity	NPC471916
0.92	High Similarity	NPC322903
0.9082	High Similarity	NPC478176
0.8932	High Similarity	NPC317107
0.8922	High Similarity	NPC87335
0.8846	High Similarity	NPC317687
0.88	High Similarity	NPC131366
0.8776	High Similarity	NPC264378
0.8283	Intermediate Similarity	NPC476245
0.8257	Intermediate Similarity	NPC270478
0.8241	Intermediate Similarity	NPC159333
0.8224	Intermediate Similarity	NPC207689
0.8191	Intermediate Similarity	NPC60951
0.8182	Intermediate Similarity	NPC196227
0.8165	Intermediate Similarity	NPC238667
0.8163	Intermediate Similarity	NPC116726
0.8155	Intermediate Similarity	NPC39996
0.81	Intermediate Similarity	NPC316215
0.8095	Intermediate Similarity	NPC1679
0.8077	Intermediate Similarity	NPC473624
0.8061	Intermediate Similarity	NPC473099
0.8061	Intermediate Similarity	NPC134321
0.8039	Intermediate Similarity	NPC216478
0.8039	Intermediate Similarity	NPC316598
0.802	Intermediate Similarity	NPC202833
0.8018	Intermediate Similarity	NPC243065
0.8018	Intermediate Similarity	NPC469684
0.8018	Intermediate Similarity	NPC474518
0.8	Intermediate Similarity	NPC296950
0.8	Intermediate Similarity	NPC72255
0.7981	Intermediate Similarity	NPC476081
0.798	Intermediate Similarity	NPC73457
0.7961	Intermediate Similarity	NPC472972
0.7959	Intermediate Similarity	NPC473100
0.7957	Intermediate Similarity	NPC172013
0.7944	Intermediate Similarity	NPC476479
0.7944	Intermediate Similarity	NPC151393
0.7941	Intermediate Similarity	NPC287668
0.7925	Intermediate Similarity	NPC472645
0.7925	Intermediate Similarity	NPC128828
0.7909	Intermediate Similarity	NPC122056
0.7909	Intermediate Similarity	NPC477266
0.7905	Intermediate Similarity	NPC159533
0.7905	Intermediate Similarity	NPC249187
0.7905	Intermediate Similarity	NPC247957
0.7895	Intermediate Similarity	NPC67569
0.7885	Intermediate Similarity	NPC470184
0.7879	Intermediate Similarity	NPC128672
0.7879	Intermediate Similarity	NPC477684
0.787	Intermediate Similarity	NPC20192
0.785	Intermediate Similarity	NPC266514
0.785	Intermediate Similarity	NPC67321
0.785	Intermediate Similarity	NPC187435
0.785	Intermediate Similarity	NPC143609
0.7835	Intermediate Similarity	NPC255143
0.783	Intermediate Similarity	NPC146731
0.783	Intermediate Similarity	NPC258532
0.7826	Intermediate Similarity	NPC23786
0.7826	Intermediate Similarity	NPC470265
0.7822	Intermediate Similarity	NPC470697
0.7818	Intermediate Similarity	NPC473877
0.781	Intermediate Similarity	NPC137430
0.78	Intermediate Similarity	NPC233345
0.78	Intermediate Similarity	NPC186363
0.78	Intermediate Similarity	NPC475441
0.7798	Intermediate Similarity	NPC5103
0.7798	Intermediate Similarity	NPC161816
0.7798	Intermediate Similarity	NPC115257
0.7788	Intermediate Similarity	NPC251310
0.7788	Intermediate Similarity	NPC186525
0.7788	Intermediate Similarity	NPC709
0.7788	Intermediate Similarity	NPC474012
0.7788	Intermediate Similarity	NPC476299
0.7788	Intermediate Similarity	NPC469551
0.7788	Intermediate Similarity	NPC46761
0.7788	Intermediate Similarity	NPC472644
0.7788	Intermediate Similarity	NPC50774
0.7788	Intermediate Similarity	NPC240509
0.7778	Intermediate Similarity	NPC472439
0.7778	Intermediate Similarity	NPC264819
0.7778	Intermediate Similarity	NPC225049
0.7778	Intermediate Similarity	NPC469916
0.7778	Intermediate Similarity	NPC102843
0.7767	Intermediate Similarity	NPC70145
0.7767	Intermediate Similarity	NPC91695
0.7767	Intermediate Similarity	NPC136781
0.7759	Intermediate Similarity	NPC469789
0.7759	Intermediate Similarity	NPC67251
0.7757	Intermediate Similarity	NPC284365
0.7757	Intermediate Similarity	NPC32006
0.7757	Intermediate Similarity	NPC85529
0.7757	Intermediate Similarity	NPC123726
0.7757	Intermediate Similarity	NPC166607
0.7757	Intermediate Similarity	NPC111952
0.7757	Intermediate Similarity	NPC257353
0.775	Intermediate Similarity	NPC476193
0.7748	Intermediate Similarity	NPC71889
0.7748	Intermediate Similarity	NPC477126
0.7745	Intermediate Similarity	NPC477437
0.7745	Intermediate Similarity	NPC272617
0.7745	Intermediate Similarity	NPC477438
0.7745	Intermediate Similarity	NPC183012
0.7742	Intermediate Similarity	NPC178852
0.7736	Intermediate Similarity	NPC120321
0.7736	Intermediate Similarity	NPC469980
0.7736	Intermediate Similarity	NPC104161
0.7736	Intermediate Similarity	NPC8196
0.7736	Intermediate Similarity	NPC118902
0.7736	Intermediate Similarity	NPC320154
0.7736	Intermediate Similarity	NPC478057
0.7736	Intermediate Similarity	NPC95899
0.7736	Intermediate Similarity	NPC99266
0.7732	Intermediate Similarity	NPC15807
0.7732	Intermediate Similarity	NPC476678
0.7732	Intermediate Similarity	NPC79573
0.7727	Intermediate Similarity	NPC146945
0.7727	Intermediate Similarity	NPC171888
0.7723	Intermediate Similarity	NPC477435
0.7723	Intermediate Similarity	NPC477436
0.7719	Intermediate Similarity	NPC476960
0.7719	Intermediate Similarity	NPC472933
0.7714	Intermediate Similarity	NPC472643
0.7714	Intermediate Similarity	NPC111292
0.7714	Intermediate Similarity	NPC472637
0.7708	Intermediate Similarity	NPC64600
0.7706	Intermediate Similarity	NPC77089
0.7706	Intermediate Similarity	NPC475922
0.77	Intermediate Similarity	NPC475823
0.77	Intermediate Similarity	NPC113393
0.77	Intermediate Similarity	NPC474209
0.7699	Intermediate Similarity	NPC167606
0.7699	Intermediate Similarity	NPC140055
0.7699	Intermediate Similarity	NPC183580
0.7699	Intermediate Similarity	NPC286528
0.7699	Intermediate Similarity	NPC20302
0.7699	Intermediate Similarity	NPC53396
0.7699	Intermediate Similarity	NPC312824
0.7699	Intermediate Similarity	NPC98249
0.7699	Intermediate Similarity	NPC470493
0.7699	Intermediate Similarity	NPC470492
0.7692	Intermediate Similarity	NPC476729
0.7692	Intermediate Similarity	NPC177232
0.7692	Intermediate Similarity	NPC24651
0.7692	Intermediate Similarity	NPC212465
0.7692	Intermediate Similarity	NPC470922
0.7692	Intermediate Similarity	NPC8374
0.7685	Intermediate Similarity	NPC473165
0.7679	Intermediate Similarity	NPC474872
0.7677	Intermediate Similarity	NPC277771
0.7677	Intermediate Similarity	NPC163296
0.7677	Intermediate Similarity	NPC307298
0.7672	Intermediate Similarity	NPC312833
0.767	Intermediate Similarity	NPC242848
0.767	Intermediate Similarity	NPC134072
0.767	Intermediate Similarity	NPC272411
0.767	Intermediate Similarity	NPC234993
0.7664	Intermediate Similarity	NPC294259
0.7664	Intermediate Similarity	NPC160843
0.7664	Intermediate Similarity	NPC118911
0.766	Intermediate Similarity	NPC281138
0.7658	Intermediate Similarity	NPC269530
0.7658	Intermediate Similarity	NPC90952
0.7658	Intermediate Similarity	NPC277769
0.7653	Intermediate Similarity	NPC202394
0.7653	Intermediate Similarity	NPC472985
0.7653	Intermediate Similarity	NPC94666
0.7653	Intermediate Similarity	NPC472986
0.7652	Intermediate Similarity	NPC474370
0.7647	Intermediate Similarity	NPC24861
0.7647	Intermediate Similarity	NPC196485
0.7647	Intermediate Similarity	NPC181393
0.7647	Intermediate Similarity	NPC38830
0.7647	Intermediate Similarity	NPC477713
0.7647	Intermediate Similarity	NPC245972
0.7647	Intermediate Similarity	NPC476859
0.7647	Intermediate Similarity	NPC477712
0.7647	Intermediate Similarity	NPC103527
0.7647	Intermediate Similarity	NPC477439
0.7647	Intermediate Similarity	NPC217624
0.7642	Intermediate Similarity	NPC273005
0.7642	Intermediate Similarity	NPC164551
0.7642	Intermediate Similarity	NPC31058
0.7642	Intermediate Similarity	NPC469606
0.7636	Intermediate Similarity	NPC235014
0.7636	Intermediate Similarity	NPC89408
0.7636	Intermediate Similarity	NPC153036
0.7634	Intermediate Similarity	NPC197659
0.7632	Intermediate Similarity	NPC284707
0.7632	Intermediate Similarity	NPC17772
0.7627	Intermediate Similarity	NPC293112
0.7624	Intermediate Similarity	NPC172101
0.7624	Intermediate Similarity	NPC26865
0.7619	Intermediate Similarity	NPC154072
0.7619	Intermediate Similarity	NPC47024
0.7619	Intermediate Similarity	NPC474718
0.7619	Intermediate Similarity	NPC174314
0.7615	Intermediate Similarity	NPC306265
0.7615	Intermediate Similarity	NPC89171

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 NPC112613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1699
0.2-0.3	3756
0.3-0.4	2277
0.4-0.5	800
0.5-0.6	241
0.6-0.7	184
0.7-0.8	4
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
0.7699	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD5211	Phase 2
0.7476	Intermediate Similarity	NPD5282	Discontinued
0.7431	Intermediate Similarity	NPD6402	Approved
0.7431	Intermediate Similarity	NPD5739	Approved
0.7431	Intermediate Similarity	NPD7128	Approved
0.7431	Intermediate Similarity	NPD6675	Approved
0.7429	Intermediate Similarity	NPD4755	Approved
0.7387	Intermediate Similarity	NPD6373	Approved
0.7387	Intermediate Similarity	NPD6372	Approved
0.7364	Intermediate Similarity	NPD5701	Approved
0.7364	Intermediate Similarity	NPD5697	Approved
0.7358	Intermediate Similarity	NPD4225	Approved
0.7339	Intermediate Similarity	NPD5141	Approved
0.7321	Intermediate Similarity	NPD4634	Approved
0.73	Intermediate Similarity	NPD3618	Phase 1
0.7297	Intermediate Similarity	NPD6899	Approved
0.7297	Intermediate Similarity	NPD6881	Approved
0.7297	Intermediate Similarity	NPD7320	Approved
0.729	Intermediate Similarity	NPD5285	Approved
0.729	Intermediate Similarity	NPD4700	Approved
0.729	Intermediate Similarity	NPD5286	Approved
0.729	Intermediate Similarity	NPD4696	Approved
0.7257	Intermediate Similarity	NPD6650	Approved
0.7257	Intermediate Similarity	NPD6649	Approved
0.7232	Intermediate Similarity	NPD6012	Approved
0.7232	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6013	Approved
0.7232	Intermediate Similarity	NPD6014	Approved
0.7203	Intermediate Similarity	NPD6059	Approved
0.7203	Intermediate Similarity	NPD6319	Approved
0.7203	Intermediate Similarity	NPD6054	Approved
0.717	Intermediate Similarity	NPD4697	Phase 3
0.7168	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7102	Approved
0.7168	Intermediate Similarity	NPD7290	Approved
0.7168	Intermediate Similarity	NPD6883	Approved
0.7156	Intermediate Similarity	NPD5225	Approved
0.7156	Intermediate Similarity	NPD4633	Approved
0.7156	Intermediate Similarity	NPD5226	Approved
0.7156	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD6015	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7640	Approved
0.713	Intermediate Similarity	NPD7639	Approved
0.7117	Intermediate Similarity	NPD6008	Approved
0.7105	Intermediate Similarity	NPD6617	Approved
0.7105	Intermediate Similarity	NPD6869	Approved
0.7105	Intermediate Similarity	NPD6847	Approved
0.7105	Intermediate Similarity	NPD8130	Phase 1
0.7103	Intermediate Similarity	NPD7902	Approved
0.7103	Intermediate Similarity	NPD6083	Phase 2
0.7103	Intermediate Similarity	NPD6084	Phase 2
0.7091	Intermediate Similarity	NPD5174	Approved
0.7091	Intermediate Similarity	NPD5175	Approved
0.7087	Intermediate Similarity	NPD4753	Phase 2
0.7083	Intermediate Similarity	NPD5988	Approved
0.7083	Intermediate Similarity	NPD6370	Approved
0.7075	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5695	Phase 3
0.7064	Intermediate Similarity	NPD5223	Approved
0.7048	Intermediate Similarity	NPD5779	Approved
0.7048	Intermediate Similarity	NPD5778	Approved
0.7048	Intermediate Similarity	NPD4202	Approved
0.7043	Intermediate Similarity	NPD6882	Approved
0.7043	Intermediate Similarity	NPD8297	Approved
0.7037	Intermediate Similarity	NPD7638	Approved
0.7037	Intermediate Similarity	NPD5696	Approved
0.703	Intermediate Similarity	NPD1694	Approved
0.7025	Intermediate Similarity	NPD8328	Phase 3
0.7018	Intermediate Similarity	NPD6371	Approved
0.7009	Intermediate Similarity	NPD5222	Approved
0.7009	Intermediate Similarity	NPD5221	Approved
0.7009	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7748	Approved
0.6967	Remote Similarity	NPD7492	Approved
0.6964	Remote Similarity	NPD4767	Approved
0.6964	Remote Similarity	NPD4768	Approved
0.6961	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7515	Phase 2
0.6944	Remote Similarity	NPD5173	Approved
0.6937	Remote Similarity	NPD4754	Approved
0.6923	Remote Similarity	NPD5328	Approved
0.6916	Remote Similarity	NPD5210	Approved
0.6916	Remote Similarity	NPD4629	Approved
0.6911	Remote Similarity	NPD6616	Approved
0.6909	Remote Similarity	NPD5344	Discontinued
0.6903	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3667	Approved
0.6887	Remote Similarity	NPD6399	Phase 3
0.6869	Remote Similarity	NPD4695	Discontinued
0.6864	Remote Similarity	NPD6274	Approved
0.6863	Remote Similarity	NPD1696	Phase 3
0.6857	Remote Similarity	NPD6698	Approved
0.6857	Remote Similarity	NPD46	Approved
0.6855	Remote Similarity	NPD7078	Approved
0.6855	Remote Similarity	NPD8293	Discontinued
0.6842	Remote Similarity	NPD5128	Approved
0.6842	Remote Similarity	NPD4730	Approved
0.6842	Remote Similarity	NPD4729	Approved
0.6838	Remote Similarity	NPD4632	Approved
0.6822	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7900	Approved
0.6807	Remote Similarity	NPD6009	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6796	Remote Similarity	NPD5279	Phase 3
0.6792	Remote Similarity	NPD5693	Phase 1
0.6792	Remote Similarity	NPD6411	Approved
0.6792	Remote Similarity	NPD6079	Approved
0.6765	Remote Similarity	NPD3665	Phase 1
0.6765	Remote Similarity	NPD3666	Approved
0.6765	Remote Similarity	NPD4786	Approved
0.6765	Remote Similarity	NPD3133	Approved
0.6748	Remote Similarity	NPD7604	Phase 2
0.6724	Remote Similarity	NPD5248	Approved
0.6724	Remote Similarity	NPD5251	Approved
0.6724	Remote Similarity	NPD5250	Approved
0.6724	Remote Similarity	NPD5247	Approved
0.6724	Remote Similarity	NPD5249	Phase 3
0.6721	Remote Similarity	NPD5983	Phase 2
0.67	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5785	Approved
0.6694	Remote Similarity	NPD7100	Approved
0.6694	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6612	Remote Similarity	NPD6314	Approved
0.6612	Remote Similarity	NPD6335	Approved
0.6612	Remote Similarity	NPD6313	Approved
0.6609	Remote Similarity	NPD6412	Phase 2
0.6609	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6101	Approved
0.6602	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4197	Approved
0.6585	Remote Similarity	NPD6909	Approved
0.6585	Remote Similarity	NPD6908	Approved
0.6581	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5169	Approved
0.6581	Remote Similarity	NPD5135	Approved
0.6552	Remote Similarity	NPD6686	Approved
0.6549	Remote Similarity	NPD7632	Discontinued
0.6538	Remote Similarity	NPD5329	Approved
0.6525	Remote Similarity	NPD5127	Approved
0.6508	Remote Similarity	NPD6336	Discontinued
0.6505	Remote Similarity	NPD6695	Phase 3
0.6484	Remote Similarity	NPD7319	Approved
0.6481	Remote Similarity	NPD7637	Suspended
0.6476	Remote Similarity	NPD5280	Approved
0.6476	Remote Similarity	NPD4623	Approved
0.6476	Remote Similarity	NPD4694	Approved
0.6476	Remote Similarity	NPD5690	Phase 2
0.6476	Remote Similarity	NPD4519	Discontinued
0.6471	Remote Similarity	NPD6053	Discontinued
0.6455	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8515	Approved
0.6452	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8516	Approved
0.6452	Remote Similarity	NPD6921	Approved
0.6452	Remote Similarity	NPD8513	Phase 3
0.6452	Remote Similarity	NPD8517	Approved
0.6449	Remote Similarity	NPD6904	Approved
0.6449	Remote Similarity	NPD6673	Approved
0.6449	Remote Similarity	NPD1695	Approved
0.6449	Remote Similarity	NPD6080	Approved
0.6446	Remote Similarity	NPD6868	Approved
0.6442	Remote Similarity	NPD3668	Phase 3
0.6423	Remote Similarity	NPD4522	Approved
0.6415	Remote Similarity	NPD3573	Approved
0.641	Remote Similarity	NPD5168	Approved
0.6408	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4221	Approved
0.6408	Remote Similarity	NPD4223	Phase 3
0.6389	Remote Similarity	NPD5692	Phase 3
0.6378	Remote Similarity	NPD7507	Approved
0.6364	Remote Similarity	NPD5167	Approved
0.6356	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6110	Phase 1
0.6337	Remote Similarity	NPD3617	Approved
0.633	Remote Similarity	NPD5284	Approved
0.633	Remote Similarity	NPD6050	Approved
0.633	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD5694	Approved
0.6321	Remote Similarity	NPD7521	Approved
0.6321	Remote Similarity	NPD5330	Approved
0.6321	Remote Similarity	NPD7334	Approved
0.6321	Remote Similarity	NPD6409	Approved
0.6321	Remote Similarity	NPD7146	Approved
0.6321	Remote Similarity	NPD6684	Approved
0.6308	Remote Similarity	NPD5956	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