NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	384.23
Volume:	423.253
LogP:	4.614
LogD:	4.207
LogS:	-4.657
# Rotatable Bonds:	8
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	4.132
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.674
MDCK Permeability:	2.593578574305866e-05
Pgp-inhibitor:	0.668
Pgp-substrate:	0.771
Human Intestinal Absorption (HIA):	0.789
20% Bioavailability (F20%):	0.141
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	97.54302215576172%
Volume Distribution (VD):	1.615
Pgp-substrate:	1.9391534328460693%

ADMET: Metabolism

CYP1A2-inhibitor:	0.302
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.415
CYP2C19-substrate:	0.767
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.384
CYP2D6-substrate:	0.531
CYP3A4-inhibitor:	0.602
CYP3A4-substrate:	0.376

ADMET: Excretion

Clearance (CL):	7.664
Half-life (T1/2):	0.061

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.535
Drug-inuced Liver Injury (DILI):	0.16
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.794
Carcinogencity:	0.038
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.489

Download Data

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

Natural Product: NPC477535

Natural Product ID:	NPC477535
*Common Name:**	mutisicoumaranone D
IUPAC Name:	2-hydroxy-2-[(2E,6E)-8-hydroxy-3,7,11-trimethyldodeca-2,6,10-trienyl]-4-methyl-1-benzofuran-3-one
Synonyms:	Mutisicoumaranone D
Standard InCHIKey:	KAPQAECQDBIIBY-MQRUAEGHSA-N
Standard InCHI:	InChI=1S/C24H32O4/c1-16(2)12-13-20(25)18(4)9-6-8-17(3)14-15-24(27)23(26)22-19(5)10-7-11-21(22)28-24/h7,9-12,14,20,25,27H,6,8,13,15H2,1-5H3/b17-14+,18-9+
SMILES:	CC1=C2C(=CC=C1)OC(C2=O)(C/C=C(\C)/CC/C=C(\C)/C(CC=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10362614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO15444	Mutisia friesiana	Species	Asteraceae	Eukaryota	aerial parts	Jujuy, Departamento de Humahuaca, Argentina	n.a.	PMID[15165137]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	10	mm	PMID[15165137]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10	mm	PMID[15165137]

☑ 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 NPC477535 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	294
0.1-0.2	1309
0.2-0.3	3244
0.3-0.4	7932
0.4-0.5	11188
0.5-0.6	3906
0.6-0.7	8815
0.7-0.8	5850
0.8-0.85	136
0.85-0.9	19
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC477537
0.9481	High Similarity	NPC477534
0.9474	High Similarity	NPC477536
0.8897	High Similarity	NPC324488
0.8832	High Similarity	NPC470160
0.8794	High Similarity	NPC477408
0.875	High Similarity	NPC469385
0.8716	High Similarity	NPC175617
0.8658	High Similarity	NPC471349
0.8658	High Similarity	NPC471347
0.8603	High Similarity	NPC470841
0.8571	High Similarity	NPC469425
0.8493	Intermediate Similarity	NPC477409
0.8489	Intermediate Similarity	NPC7012
0.8483	Intermediate Similarity	NPC329493
0.8451	Intermediate Similarity	NPC232996
0.844	Intermediate Similarity	NPC477210
0.8389	Intermediate Similarity	NPC219560
0.8369	Intermediate Similarity	NPC470871
0.8367	Intermediate Similarity	NPC10302
0.8367	Intermediate Similarity	NPC105381
0.8357	Intermediate Similarity	NPC477412
0.8333	Intermediate Similarity	NPC469416
0.8333	Intermediate Similarity	NPC228906
0.8333	Intermediate Similarity	NPC471348
0.8333	Intermediate Similarity	NPC98395
0.8298	Intermediate Similarity	NPC477406
0.8255	Intermediate Similarity	NPC308799
0.8252	Intermediate Similarity	NPC22222
0.8252	Intermediate Similarity	NPC217914
0.8252	Intermediate Similarity	NPC281513
0.8252	Intermediate Similarity	NPC298900
0.8248	Intermediate Similarity	NPC470162
0.8248	Intermediate Similarity	NPC470163
0.8243	Intermediate Similarity	NPC274085
0.8243	Intermediate Similarity	NPC89664
0.8227	Intermediate Similarity	NPC205360
0.8219	Intermediate Similarity	NPC475063
0.8219	Intermediate Similarity	NPC475044
0.8207	Intermediate Similarity	NPC474943
0.8207	Intermediate Similarity	NPC475005
0.8201	Intermediate Similarity	NPC319422
0.8201	Intermediate Similarity	NPC477212
0.8201	Intermediate Similarity	NPC477214
0.8201	Intermediate Similarity	NPC477211
0.82	Intermediate Similarity	NPC210320
0.82	Intermediate Similarity	NPC113428
0.82	Intermediate Similarity	NPC61284
0.82	Intermediate Similarity	NPC252208
0.8194	Intermediate Similarity	NPC317900
0.8194	Intermediate Similarity	NPC476404
0.8194	Intermediate Similarity	NPC294300
0.8194	Intermediate Similarity	NPC177742
0.8194	Intermediate Similarity	NPC64157
0.8194	Intermediate Similarity	NPC278832
0.8188	Intermediate Similarity	NPC167055
0.8188	Intermediate Similarity	NPC240744
0.8188	Intermediate Similarity	NPC71210
0.8182	Intermediate Similarity	NPC474097
0.8176	Intermediate Similarity	NPC51106
0.8176	Intermediate Similarity	NPC476310
0.8176	Intermediate Similarity	NPC476164
0.8151	Intermediate Similarity	NPC268691
0.8151	Intermediate Similarity	NPC475045
0.8146	Intermediate Similarity	NPC73411
0.8146	Intermediate Similarity	NPC215711
0.8143	Intermediate Similarity	NPC201419
0.8138	Intermediate Similarity	NPC301341
0.8117	Intermediate Similarity	NPC470331
0.8112	Intermediate Similarity	NPC43627
0.8108	Intermediate Similarity	NPC474385
0.8108	Intermediate Similarity	NPC133585
0.8108	Intermediate Similarity	NPC96692
0.8105	Intermediate Similarity	NPC200773
0.8105	Intermediate Similarity	NPC240768
0.8099	Intermediate Similarity	NPC474143
0.8099	Intermediate Similarity	NPC474246
0.8099	Intermediate Similarity	NPC473982
0.8089	Intermediate Similarity	NPC313368
0.8085	Intermediate Similarity	NPC939
0.8085	Intermediate Similarity	NPC59654
0.8082	Intermediate Similarity	NPC475028
0.8082	Intermediate Similarity	NPC476025
0.8079	Intermediate Similarity	NPC259632
0.8079	Intermediate Similarity	NPC472036
0.8077	Intermediate Similarity	NPC104380
0.8077	Intermediate Similarity	NPC217602
0.8077	Intermediate Similarity	NPC473282
0.8065	Intermediate Similarity	NPC99381
0.8058	Intermediate Similarity	NPC477213
0.8058	Intermediate Similarity	NPC287473
0.8056	Intermediate Similarity	NPC265793
0.8054	Intermediate Similarity	NPC472006
0.8054	Intermediate Similarity	NPC158871
0.8052	Intermediate Similarity	NPC474843
0.8052	Intermediate Similarity	NPC473967
0.8042	Intermediate Similarity	NPC118253
0.8041	Intermediate Similarity	NPC244923
0.8041	Intermediate Similarity	NPC1704
0.8041	Intermediate Similarity	NPC67650
0.8039	Intermediate Similarity	NPC473966
0.8028	Intermediate Similarity	NPC475880
0.8026	Intermediate Similarity	NPC240622
0.8026	Intermediate Similarity	NPC240253
0.8026	Intermediate Similarity	NPC471641
0.8026	Intermediate Similarity	NPC471642
0.8015	Intermediate Similarity	NPC470092
0.8014	Intermediate Similarity	NPC121243
0.8014	Intermediate Similarity	NPC284184
0.8014	Intermediate Similarity	NPC240147
0.8013	Intermediate Similarity	NPC469507
0.8013	Intermediate Similarity	NPC471346
0.8013	Intermediate Similarity	NPC164244
0.8013	Intermediate Similarity	NPC107625
0.8	Intermediate Similarity	NPC280404
0.8	Intermediate Similarity	NPC316262
0.8	Intermediate Similarity	NPC51037
0.8	Intermediate Similarity	NPC277426
0.8	Intermediate Similarity	NPC27407
0.8	Intermediate Similarity	NPC210425
0.8	Intermediate Similarity	NPC314653
0.8	Intermediate Similarity	NPC301233
0.8	Intermediate Similarity	NPC306816
0.8	Intermediate Similarity	NPC193200
0.8	Intermediate Similarity	NPC142027
0.8	Intermediate Similarity	NPC185103
0.8	Intermediate Similarity	NPC86373
0.7987	Intermediate Similarity	NPC61594
0.7987	Intermediate Similarity	NPC146837
0.7987	Intermediate Similarity	NPC39819
0.7987	Intermediate Similarity	NPC310128
0.7987	Intermediate Similarity	NPC216752
0.7987	Intermediate Similarity	NPC471613
0.7987	Intermediate Similarity	NPC56735
0.7987	Intermediate Similarity	NPC278329
0.7987	Intermediate Similarity	NPC469579
0.7987	Intermediate Similarity	NPC197461
0.7985	Intermediate Similarity	NPC477453
0.7975	Intermediate Similarity	NPC306978
0.7974	Intermediate Similarity	NPC226578
0.7973	Intermediate Similarity	NPC473499
0.7972	Intermediate Similarity	NPC15083
0.7972	Intermediate Similarity	NPC141549
0.7962	Intermediate Similarity	NPC161650
0.7961	Intermediate Similarity	NPC478163
0.7961	Intermediate Similarity	NPC478018
0.7961	Intermediate Similarity	NPC14098
0.7961	Intermediate Similarity	NPC71055
0.7959	Intermediate Similarity	NPC287068
0.7959	Intermediate Similarity	NPC173980
0.7958	Intermediate Similarity	NPC271832
0.7947	Intermediate Similarity	NPC97662
0.7947	Intermediate Similarity	NPC47152
0.7947	Intermediate Similarity	NPC473951
0.7947	Intermediate Similarity	NPC472034
0.7945	Intermediate Similarity	NPC473268
0.7937	Intermediate Similarity	NPC147596
0.7935	Intermediate Similarity	NPC281272
0.7935	Intermediate Similarity	NPC275878
0.7935	Intermediate Similarity	NPC207624
0.7935	Intermediate Similarity	NPC183536
0.7935	Intermediate Similarity	NPC142308
0.7935	Intermediate Similarity	NPC253904
0.7935	Intermediate Similarity	NPC321363
0.7935	Intermediate Similarity	NPC34965
0.7933	Intermediate Similarity	NPC257404
0.7933	Intermediate Similarity	NPC469542
0.7933	Intermediate Similarity	NPC471520
0.7929	Intermediate Similarity	NPC224657
0.7922	Intermediate Similarity	NPC469670
0.7922	Intermediate Similarity	NPC475717
0.7922	Intermediate Similarity	NPC469619
0.7919	Intermediate Similarity	NPC90411
0.7919	Intermediate Similarity	NPC471444
0.7919	Intermediate Similarity	NPC475730
0.7914	Intermediate Similarity	NPC315306
0.7914	Intermediate Similarity	NPC93730
0.7914	Intermediate Similarity	NPC313717
0.7911	Intermediate Similarity	NPC279732
0.7908	Intermediate Similarity	NPC228012
0.7905	Intermediate Similarity	NPC471602
0.7905	Intermediate Similarity	NPC256463
0.7905	Intermediate Similarity	NPC111422
0.7905	Intermediate Similarity	NPC216312
0.7905	Intermediate Similarity	NPC299405
0.7905	Intermediate Similarity	NPC306835
0.7905	Intermediate Similarity	NPC29771
0.7905	Intermediate Similarity	NPC476477
0.7902	Intermediate Similarity	NPC282230
0.7902	Intermediate Similarity	NPC7569
0.7902	Intermediate Similarity	NPC183348
0.7902	Intermediate Similarity	NPC278787
0.7901	Intermediate Similarity	NPC63470
0.7898	Intermediate Similarity	NPC154341
0.7898	Intermediate Similarity	NPC478223
0.7895	Intermediate Similarity	NPC60389
0.7895	Intermediate Similarity	NPC85734
0.7895	Intermediate Similarity	NPC211565
0.7895	Intermediate Similarity	NPC301949
0.7895	Intermediate Similarity	NPC206579

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 NPC477535 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	893
0.2-0.3	1578
0.3-0.4	2414
0.4-0.5	2091
0.5-0.6	1230
0.6-0.7	548
0.7-0.8	130
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
0.8082	Intermediate Similarity	NPD2346	Discontinued
0.8	Intermediate Similarity	NPD2798	Approved
0.7862	Intermediate Similarity	NPD6355	Discontinued
0.7842	Intermediate Similarity	NPD9717	Approved
0.7823	Intermediate Similarity	NPD2799	Discontinued
0.7778	Intermediate Similarity	NPD2313	Discontinued
0.7771	Intermediate Similarity	NPD7819	Suspended
0.777	Intermediate Similarity	NPD2935	Discontinued
0.777	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD6832	Phase 2
0.7742	Intermediate Similarity	NPD3226	Approved
0.774	Intermediate Similarity	NPD447	Suspended
0.7722	Intermediate Similarity	NPD5402	Approved
0.7718	Intermediate Similarity	NPD2344	Approved
0.7718	Intermediate Similarity	NPD1471	Phase 3
0.7712	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2534	Approved
0.7712	Intermediate Similarity	NPD2533	Approved
0.7712	Intermediate Similarity	NPD2532	Approved
0.7673	Intermediate Similarity	NPD3882	Suspended
0.7658	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD411	Approved
0.7636	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7075	Discontinued
0.7619	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD5403	Approved
0.7605	Intermediate Similarity	NPD7251	Discontinued
0.76	Intermediate Similarity	NPD5762	Approved
0.76	Intermediate Similarity	NPD5763	Approved
0.76	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6844	Discontinued
0.7576	Intermediate Similarity	NPD3818	Discontinued
0.7571	Intermediate Similarity	NPD3496	Discontinued
0.7566	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7808	Phase 3
0.7552	Intermediate Similarity	NPD1203	Approved
0.7551	Intermediate Similarity	NPD4060	Phase 1
0.755	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6273	Approved
0.7547	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6797	Phase 2
0.7534	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6798	Discontinued
0.7532	Intermediate Similarity	NPD6799	Approved
0.7516	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2309	Approved
0.7515	Intermediate Similarity	NPD8313	Approved
0.7515	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD5647	Approved
0.75	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7484	Intermediate Similarity	NPD6801	Discontinued
0.7484	Intermediate Similarity	NPD1934	Approved
0.7484	Intermediate Similarity	NPD5401	Approved
0.7483	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6005	Phase 3
0.7483	Intermediate Similarity	NPD6004	Phase 3
0.7483	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6599	Discontinued
0.7455	Intermediate Similarity	NPD6166	Phase 2
0.7455	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4628	Phase 3
0.745	Intermediate Similarity	NPD6653	Approved
0.7434	Intermediate Similarity	NPD1549	Phase 2
0.7431	Intermediate Similarity	NPD2797	Approved
0.7425	Intermediate Similarity	NPD7054	Approved
0.7417	Intermediate Similarity	NPD2796	Approved
0.7415	Intermediate Similarity	NPD3268	Approved
0.7414	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7472	Approved
0.7378	Intermediate Similarity	NPD6959	Discontinued
0.7376	Intermediate Similarity	NPD4626	Approved
0.7365	Intermediate Similarity	NPD3751	Discontinued
0.7353	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD3750	Approved
0.7338	Intermediate Similarity	NPD9493	Approved
0.7338	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.7325	Intermediate Similarity	NPD1512	Approved
0.7305	Intermediate Similarity	NPD5691	Approved
0.7303	Intermediate Similarity	NPD1551	Phase 2
0.7296	Intermediate Similarity	NPD2651	Approved
0.7296	Intermediate Similarity	NPD2649	Approved
0.7273	Intermediate Similarity	NPD1201	Approved
0.7273	Intermediate Similarity	NPD2800	Approved
0.7267	Intermediate Similarity	NPD1933	Approved
0.7266	Intermediate Similarity	NPD6671	Approved
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4661	Approved
0.7261	Intermediate Similarity	NPD4662	Approved
0.7254	Intermediate Similarity	NPD1778	Approved
0.725	Intermediate Similarity	NPD4380	Phase 2
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.7246	Intermediate Similarity	NPD1241	Discontinued
0.7241	Intermediate Similarity	NPD1876	Approved
0.7239	Intermediate Similarity	NPD7768	Phase 2
0.7237	Intermediate Similarity	NPD1510	Phase 2
0.7237	Intermediate Similarity	NPD4308	Phase 3
0.723	Intermediate Similarity	NPD7095	Approved
0.7222	Intermediate Similarity	NPD2801	Approved
0.7222	Intermediate Similarity	NPD1608	Approved
0.7212	Intermediate Similarity	NPD5494	Approved
0.7208	Intermediate Similarity	NPD2897	Discontinued
0.7205	Intermediate Similarity	NPD7411	Suspended
0.72	Intermediate Similarity	NPD1240	Approved
0.7197	Intermediate Similarity	NPD1511	Approved
0.7195	Intermediate Similarity	NPD3749	Approved
0.7192	Intermediate Similarity	NPD6362	Approved
0.7192	Intermediate Similarity	NPD1470	Approved
0.719	Intermediate Similarity	NPD4476	Approved
0.719	Intermediate Similarity	NPD4477	Approved
0.7188	Intermediate Similarity	NPD7458	Discontinued
0.7184	Intermediate Similarity	NPD8434	Phase 2
0.7153	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD919	Approved
0.7133	Intermediate Similarity	NPD8032	Phase 2
0.7133	Intermediate Similarity	NPD4062	Phase 3
0.7124	Intermediate Similarity	NPD3748	Approved
0.7123	Intermediate Similarity	NPD6696	Suspended
0.7123	Intermediate Similarity	NPD1283	Approved
0.7118	Intermediate Similarity	NPD5844	Phase 1
0.7115	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7003	Approved
0.7105	Intermediate Similarity	NPD1607	Approved
0.7102	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7473	Discontinued
0.7097	Intermediate Similarity	NPD2424	Discontinued
0.7089	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2979	Phase 3
0.7086	Intermediate Similarity	NPD4140	Approved
0.7083	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6100	Approved
0.7078	Intermediate Similarity	NPD6099	Approved
0.7075	Intermediate Similarity	NPD3266	Approved
0.7075	Intermediate Similarity	NPD3267	Approved
0.707	Intermediate Similarity	NPD3887	Approved
0.7067	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3764	Approved
0.7066	Intermediate Similarity	NPD1247	Approved
0.7063	Intermediate Similarity	NPD1651	Approved
0.7063	Intermediate Similarity	NPD5585	Approved
0.7063	Intermediate Similarity	NPD920	Approved
0.7055	Intermediate Similarity	NPD37	Approved
0.7044	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4965	Approved
0.703	Intermediate Similarity	NPD4967	Phase 2
0.703	Intermediate Similarity	NPD4966	Approved
0.7024	Intermediate Similarity	NPD5710	Approved
0.7024	Intermediate Similarity	NPD6232	Discontinued
0.7024	Intermediate Similarity	NPD5711	Approved
0.7021	Intermediate Similarity	NPD7157	Approved
0.7014	Intermediate Similarity	NPD17	Approved
0.7012	Intermediate Similarity	NPD5760	Phase 2
0.7012	Intermediate Similarity	NPD5761	Phase 2
0.7011	Intermediate Similarity	NPD7435	Discontinued
0.7006	Intermediate Similarity	NPD4110	Phase 3
0.7006	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5049	Phase 3
0.6987	Remote Similarity	NPD5958	Discontinued
0.6987	Remote Similarity	NPD4534	Discontinued
0.6986	Remote Similarity	NPD3972	Approved
0.6982	Remote Similarity	NPD3926	Phase 2
0.698	Remote Similarity	NPD1712	Approved
0.698	Remote Similarity	NPD2861	Phase 2
0.6974	Remote Similarity	NPD4307	Phase 2
0.697	Remote Similarity	NPD7318	Phase 3
0.697	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2296	Approved
0.6968	Remote Similarity	NPD6032	Approved
0.6964	Remote Similarity	NPD7199	Phase 2
0.6964	Remote Similarity	NPD8127	Discontinued
0.6962	Remote Similarity	NPD2354	Approved
0.6959	Remote Similarity	NPD2163	Approved
0.6951	Remote Similarity	NPD6279	Approved
0.6951	Remote Similarity	NPD6280	Approved
0.695	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7097	Phase 1
0.6943	Remote Similarity	NPD1243	Approved
0.6941	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.694	Remote Similarity	NPD6780	Approved
0.694	Remote Similarity	NPD6779	Approved
0.694	Remote Similarity	NPD6778	Approved
0.694	Remote Similarity	NPD6781	Approved
0.694	Remote Similarity	NPD6777	Approved
0.694	Remote Similarity	NPD6776	Approved
0.694	Remote Similarity	NPD6782	Approved
0.6937	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD642	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