NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	350.785
LogP:	3.652
LogD:	3.012
LogS:	-4.201
# Rotatable Bonds:	3
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.573
Synthetic Accessibility Score:	4.883
Fsp3:	0.6
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:	-4.827
MDCK Permeability:	1.2685406545642763e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.983
30% Bioavailability (F30%):	0.509

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.073
Plasma Protein Binding (PPB):	75.5101318359375%
Volume Distribution (VD):	1.866
Pgp-substrate:	27.88785743713379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.885
CYP1A2-substrate:	0.349
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.734
CYP2C9-inhibitor:	0.677
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.17
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.343

ADMET: Excretion

Clearance (CL):	9.096
Half-life (T1/2):	0.35

ADMET: Toxicity

hERG Blockers:	0.62
Human Hepatotoxicity (H-HT):	0.878
Drug-inuced Liver Injury (DILI):	0.581
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.818
Maximum Recommended Daily Dose:	0.539
Skin Sensitization:	0.801
Carcinogencity:	0.1
Eye Corrosion:	0.035
Eye Irritation:	0.029
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC477130

Natural Product ID:	NPC477130
*Common Name:**	Oopodin
IUPAC Name:	[(3R,3aS,5aS,6R,9aR,9bR)-3,5a-dimethyl-9-methylidene-2-oxo-3a,4,5,6,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-6-yl] (E)-2-methylbut-2-enoate
Synonyms:	Oopodin
Standard InCHIKey:	AOKVPXZYQSAPMF-CFXDCANBSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-6-11(2)18(21)23-15-8-7-12(3)16-17-14(9-10-20(15,16)5)13(4)19(22)24-17/h6-8,13-17H,3,9-10H2,1-2,4-5H3/b11-6+/t13-,14+,15-,16+,17-,20-/m1/s1
SMILES:	C/C=C(\C)/C(=O)O[C@@H]1C=CC(=C)[C@@H]2[C@@]1(CC[C@@H]3[C@H]2OC(=O)[C@@H]3C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	40530726
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO33550	Ferula varia	Species	Apiaceae	Eukaryota	roots	Kyzylkum, Uzbekistan	2001-APR	PMID[18052129]

☑ 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	5

Activity Type	# Activity
Cell Line	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	34.7	ug/ml	PMID[18052129]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	35.1	ug/ml	PMID[18052129]
NPT2	Others	Unspecified		IC50	=	24.7	ug/ml	PMID[18052129]
NPT2	Others	Unspecified		IC50	=	13.8	ug/ml	PMID[18052129]
NPT2	Others	Unspecified		IC50	=	25.4	ug/ml	PMID[18052129]

☑ 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 NPC477130 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	207
0.1-0.2	962
0.2-0.3	3656
0.3-0.4	8376
0.4-0.5	13446
0.5-0.6	7678
0.6-0.7	6082
0.7-0.8	2086
0.8-0.85	163
0.85-0.9	33
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477129
0.9425	High Similarity	NPC477128
0.9213	High Similarity	NPC220454
0.9213	High Similarity	NPC469595
0.9213	High Similarity	NPC212679
0.9205	High Similarity	NPC215831
0.9101	High Similarity	NPC73995
0.9	High Similarity	NPC469372
0.8989	High Similarity	NPC226863
0.8969	High Similarity	NPC477125
0.8913	High Similarity	NPC38830
0.8889	High Similarity	NPC284561
0.8864	High Similarity	NPC177932
0.8851	High Similarity	NPC22611
0.8817	High Similarity	NPC183012
0.8804	High Similarity	NPC475657
0.8791	High Similarity	NPC152467
0.8723	High Similarity	NPC112654
0.871	High Similarity	NPC470697
0.8696	High Similarity	NPC186363
0.8696	High Similarity	NPC65513
0.8696	High Similarity	NPC233345
0.8681	High Similarity	NPC173042
0.866	High Similarity	NPC31058
0.866	High Similarity	NPC469606
0.866	High Similarity	NPC273005
0.8652	High Similarity	NPC189311
0.8632	High Similarity	NPC38530
0.8632	High Similarity	NPC84335
0.8632	High Similarity	NPC110937
0.8621	High Similarity	NPC38642
0.8586	High Similarity	NPC469607
0.8571	High Similarity	NPC471365
0.8571	High Similarity	NPC254202
0.8571	High Similarity	NPC132395
0.8571	High Similarity	NPC471364
0.8539	High Similarity	NPC159635
0.8539	High Similarity	NPC139566
0.8523	High Similarity	NPC178676
0.8523	High Similarity	NPC186276
0.8506	High Similarity	NPC195424
0.8495	Intermediate Similarity	NPC49420
0.8485	Intermediate Similarity	NPC470297
0.8478	Intermediate Similarity	NPC168131
0.8478	Intermediate Similarity	NPC288699
0.8438	Intermediate Similarity	NPC2049
0.8427	Intermediate Similarity	NPC193198
0.8427	Intermediate Similarity	NPC118423
0.8421	Intermediate Similarity	NPC295347
0.8409	Intermediate Similarity	NPC475665
0.8387	Intermediate Similarity	NPC474842
0.8387	Intermediate Similarity	NPC475965
0.837	Intermediate Similarity	NPC472302
0.837	Intermediate Similarity	NPC277771
0.8367	Intermediate Similarity	NPC168319
0.8367	Intermediate Similarity	NPC194028
0.8367	Intermediate Similarity	NPC244456
0.8367	Intermediate Similarity	NPC469657
0.8352	Intermediate Similarity	NPC220478
0.8352	Intermediate Similarity	NPC168248
0.8351	Intermediate Similarity	NPC57079
0.8351	Intermediate Similarity	NPC216478
0.8351	Intermediate Similarity	NPC176845
0.8351	Intermediate Similarity	NPC252295
0.8351	Intermediate Similarity	NPC316598
0.8351	Intermediate Similarity	NPC108368
0.835	Intermediate Similarity	NPC179798
0.835	Intermediate Similarity	NPC304180
0.8333	Intermediate Similarity	NPC311166
0.8333	Intermediate Similarity	NPC30486
0.8333	Intermediate Similarity	NPC470011
0.8333	Intermediate Similarity	NPC228477
0.8333	Intermediate Similarity	NPC307164
0.8333	Intermediate Similarity	NPC137911
0.8317	Intermediate Similarity	NPC133422
0.8316	Intermediate Similarity	NPC471446
0.8316	Intermediate Similarity	NPC474841
0.8316	Intermediate Similarity	NPC473434
0.8315	Intermediate Similarity	NPC226988
0.8315	Intermediate Similarity	NPC268122
0.8315	Intermediate Similarity	NPC200513
0.83	Intermediate Similarity	NPC189616
0.8298	Intermediate Similarity	NPC252433
0.8298	Intermediate Similarity	NPC72845
0.8283	Intermediate Similarity	NPC155332
0.8283	Intermediate Similarity	NPC114540
0.8283	Intermediate Similarity	NPC32577
0.828	Intermediate Similarity	NPC5509
0.8265	Intermediate Similarity	NPC47024
0.8265	Intermediate Similarity	NPC470906
0.8265	Intermediate Similarity	NPC473219
0.8265	Intermediate Similarity	NPC470761
0.8265	Intermediate Similarity	NPC476299
0.8265	Intermediate Similarity	NPC474012
0.8261	Intermediate Similarity	NPC181327
0.8261	Intermediate Similarity	NPC175293
0.8247	Intermediate Similarity	NPC70145
0.8247	Intermediate Similarity	NPC474343
0.8247	Intermediate Similarity	NPC208094
0.8247	Intermediate Similarity	NPC204054
0.8247	Intermediate Similarity	NPC257726
0.8247	Intermediate Similarity	NPC91695
0.8247	Intermediate Similarity	NPC202705
0.8242	Intermediate Similarity	NPC110405
0.8235	Intermediate Similarity	NPC275539
0.8235	Intermediate Similarity	NPC189075
0.8229	Intermediate Similarity	NPC209355
0.8229	Intermediate Similarity	NPC33473
0.8211	Intermediate Similarity	NPC162615
0.8211	Intermediate Similarity	NPC166346
0.8211	Intermediate Similarity	NPC139692
0.8211	Intermediate Similarity	NPC152778
0.8211	Intermediate Similarity	NPC205034
0.8191	Intermediate Similarity	NPC475776
0.8191	Intermediate Similarity	NPC8062
0.8191	Intermediate Similarity	NPC310479
0.819	Intermediate Similarity	NPC469463
0.819	Intermediate Similarity	NPC469496
0.819	Intermediate Similarity	NPC56448
0.819	Intermediate Similarity	NPC469454
0.8182	Intermediate Similarity	NPC472637
0.8172	Intermediate Similarity	NPC24816
0.8172	Intermediate Similarity	NPC477302
0.8163	Intermediate Similarity	NPC23364
0.8161	Intermediate Similarity	NPC187568
0.8161	Intermediate Similarity	NPC41780
0.8155	Intermediate Similarity	NPC112457
0.8155	Intermediate Similarity	NPC469370
0.8152	Intermediate Similarity	NPC85698
0.8152	Intermediate Similarity	NPC250981
0.8152	Intermediate Similarity	NPC6979
0.8152	Intermediate Similarity	NPC185638
0.8137	Intermediate Similarity	NPC110496
0.8132	Intermediate Similarity	NPC219011
0.8125	Intermediate Similarity	NPC88507
0.8125	Intermediate Similarity	NPC57117
0.8125	Intermediate Similarity	NPC84893
0.8119	Intermediate Similarity	NPC118911
0.8119	Intermediate Similarity	NPC146731
0.8111	Intermediate Similarity	NPC471218
0.8111	Intermediate Similarity	NPC94200
0.8105	Intermediate Similarity	NPC303697
0.8105	Intermediate Similarity	NPC473944
0.81	Intermediate Similarity	NPC476081
0.81	Intermediate Similarity	NPC235369
0.809	Intermediate Similarity	NPC268827
0.8085	Intermediate Similarity	NPC36668
0.8085	Intermediate Similarity	NPC177141
0.8085	Intermediate Similarity	NPC474396
0.8085	Intermediate Similarity	NPC206001
0.8085	Intermediate Similarity	NPC50488
0.8085	Intermediate Similarity	NPC218927
0.8085	Intermediate Similarity	NPC118011
0.8085	Intermediate Similarity	NPC474844
0.8081	Intermediate Similarity	NPC266955
0.8081	Intermediate Similarity	NPC473204
0.8081	Intermediate Similarity	NPC476303
0.8077	Intermediate Similarity	NPC5103
0.8077	Intermediate Similarity	NPC253906
0.8068	Intermediate Similarity	NPC35574
0.8068	Intermediate Similarity	NPC184737
0.8065	Intermediate Similarity	NPC305029
0.8065	Intermediate Similarity	NPC312561
0.8065	Intermediate Similarity	NPC477228
0.8061	Intermediate Similarity	NPC292133
0.8061	Intermediate Similarity	NPC121402
0.8061	Intermediate Similarity	NPC151681
0.8061	Intermediate Similarity	NPC224356
0.8061	Intermediate Similarity	NPC10057
0.8061	Intermediate Similarity	NPC132753
0.8061	Intermediate Similarity	NPC472188
0.8061	Intermediate Similarity	NPC175351
0.8061	Intermediate Similarity	NPC226986
0.8058	Intermediate Similarity	NPC476802
0.8058	Intermediate Similarity	NPC89171
0.8046	Intermediate Similarity	NPC41017
0.8043	Intermediate Similarity	NPC52628
0.8043	Intermediate Similarity	NPC65661
0.8041	Intermediate Similarity	NPC474909
0.8041	Intermediate Similarity	NPC473369
0.8039	Intermediate Similarity	NPC266570
0.8039	Intermediate Similarity	NPC252296
0.8039	Intermediate Similarity	NPC478208
0.8039	Intermediate Similarity	NPC34768
0.8022	Intermediate Similarity	NPC194637
0.8021	Intermediate Similarity	NPC79117
0.8021	Intermediate Similarity	NPC474185
0.8021	Intermediate Similarity	NPC1108
0.8021	Intermediate Similarity	NPC115021
0.802	Intermediate Similarity	NPC176883
0.802	Intermediate Similarity	NPC473283
0.802	Intermediate Similarity	NPC475526
0.802	Intermediate Similarity	NPC476237
0.802	Intermediate Similarity	NPC329345
0.8	Intermediate Similarity	NPC115899
0.8	Intermediate Similarity	NPC63249
0.8	Intermediate Similarity	NPC221111
0.8	Intermediate Similarity	NPC81530
0.8	Intermediate Similarity	NPC224720
0.8	Intermediate Similarity	NPC182136

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 NPC477130 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1143
0.2-0.3	3459
0.3-0.4	2713
0.4-0.5	1095
0.5-0.6	303
0.6-0.7	197
0.7-0.8	69
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8864	High Similarity	NPD1694	Approved
0.8315	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4225	Approved
0.7755	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7900	Approved
0.7629	Intermediate Similarity	NPD5207	Approved
0.7579	Intermediate Similarity	NPD7146	Approved
0.7579	Intermediate Similarity	NPD7334	Approved
0.7579	Intermediate Similarity	NPD5330	Approved
0.7579	Intermediate Similarity	NPD7521	Approved
0.7579	Intermediate Similarity	NPD6409	Approved
0.7579	Intermediate Similarity	NPD6684	Approved
0.7528	Intermediate Similarity	NPD8039	Approved
0.7525	Intermediate Similarity	NPD7902	Approved
0.7524	Intermediate Similarity	NPD6008	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3573	Approved
0.7477	Intermediate Similarity	NPD7115	Discovery
0.7475	Intermediate Similarity	NPD6399	Phase 3
0.7451	Intermediate Similarity	NPD7638	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6903	Approved
0.7423	Intermediate Similarity	NPD5737	Approved
0.7423	Intermediate Similarity	NPD6672	Approved
0.74	Intermediate Similarity	NPD7748	Approved
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7374	Intermediate Similarity	NPD5693	Phase 1
0.7374	Intermediate Similarity	NPD5281	Approved
0.7374	Intermediate Similarity	NPD5284	Approved
0.7374	Intermediate Similarity	NPD5694	Approved
0.734	Intermediate Similarity	NPD5209	Approved
0.7327	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD5692	Phase 3
0.7228	Intermediate Similarity	NPD6001	Approved
0.7222	Intermediate Similarity	NPD6011	Approved
0.7222	Intermediate Similarity	NPD6881	Approved
0.7222	Intermediate Similarity	NPD6899	Approved
0.7216	Intermediate Similarity	NPD3618	Phase 1
0.72	Intermediate Similarity	NPD6050	Approved
0.72	Intermediate Similarity	NPD7515	Phase 2
0.72	Intermediate Similarity	NPD6411	Approved
0.7182	Intermediate Similarity	NPD6649	Approved
0.7182	Intermediate Similarity	NPD6650	Approved
0.7156	Intermediate Similarity	NPD6012	Approved
0.7156	Intermediate Similarity	NPD6013	Approved
0.7156	Intermediate Similarity	NPD6014	Approved
0.7129	Intermediate Similarity	NPD5779	Approved
0.7129	Intermediate Similarity	NPD5778	Approved
0.71	Intermediate Similarity	NPD5785	Approved
0.7091	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6883	Approved
0.7091	Intermediate Similarity	NPD7102	Approved
0.7091	Intermediate Similarity	NPD7290	Approved
0.7064	Intermediate Similarity	NPD6686	Approved
0.7037	Intermediate Similarity	NPD6402	Approved
0.7037	Intermediate Similarity	NPD7128	Approved
0.7037	Intermediate Similarity	NPD5739	Approved
0.7037	Intermediate Similarity	NPD6675	Approved
0.703	Intermediate Similarity	NPD6079	Approved
0.7027	Intermediate Similarity	NPD6847	Approved
0.7027	Intermediate Similarity	NPD8130	Phase 1
0.7027	Intermediate Similarity	NPD6617	Approved
0.7027	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD6051	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6373	Approved
0.699	Remote Similarity	NPD5695	Phase 3
0.6972	Remote Similarity	NPD5701	Approved
0.6964	Remote Similarity	NPD8297	Approved
0.6964	Remote Similarity	NPD6882	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD5222	Approved
0.6916	Remote Similarity	NPD5211	Phase 2
0.6909	Remote Similarity	NPD7320	Approved
0.69	Remote Similarity	NPD5208	Approved
0.6887	Remote Similarity	NPD5286	Approved
0.6887	Remote Similarity	NPD4696	Approved
0.6887	Remote Similarity	NPD6648	Approved
0.6887	Remote Similarity	NPD5285	Approved
0.6869	Remote Similarity	NPD5279	Phase 3
0.6869	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD8034	Phase 2
0.6863	Remote Similarity	NPD8035	Phase 2
0.6857	Remote Similarity	NPD6083	Phase 2
0.6857	Remote Similarity	NPD5173	Approved
0.6857	Remote Similarity	NPD6084	Phase 2
0.6848	Remote Similarity	NPD4058	Approved
0.6837	Remote Similarity	NPD3666	Approved
0.6837	Remote Similarity	NPD3668	Phase 3
0.6837	Remote Similarity	NPD3133	Approved
0.6837	Remote Similarity	NPD3665	Phase 1
0.6832	Remote Similarity	NPD1695	Approved
0.6832	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5328	Approved
0.6829	Remote Similarity	NPD7260	Phase 2
0.6827	Remote Similarity	NPD5654	Approved
0.6822	Remote Similarity	NPD5223	Approved
0.6804	Remote Similarity	NPD3667	Approved
0.6796	Remote Similarity	NPD4202	Approved
0.6789	Remote Similarity	NPD5141	Approved
0.678	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4695	Discontinued
0.6762	Remote Similarity	NPD4697	Phase 3
0.6759	Remote Similarity	NPD5224	Approved
0.6759	Remote Similarity	NPD5226	Approved
0.6759	Remote Similarity	NPD5225	Approved
0.6759	Remote Similarity	NPD4633	Approved
0.6759	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD4632	Approved
0.6726	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6317	Approved
0.67	Remote Similarity	NPD4519	Discontinued
0.67	Remote Similarity	NPD6098	Approved
0.67	Remote Similarity	NPD4623	Approved
0.6699	Remote Similarity	NPD7637	Suspended
0.6698	Remote Similarity	NPD5959	Approved
0.6698	Remote Similarity	NPD4755	Approved
0.6697	Remote Similarity	NPD5174	Approved
0.6697	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6639	Remote Similarity	NPD7503	Approved
0.6638	Remote Similarity	NPD6868	Approved
0.6638	Remote Similarity	NPD6274	Approved
0.6636	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7101	Approved
0.661	Remote Similarity	NPD7100	Approved
0.6602	Remote Similarity	NPD6698	Approved
0.6602	Remote Similarity	NPD7838	Discovery
0.6602	Remote Similarity	NPD46	Approved
0.66	Remote Similarity	NPD5363	Approved
0.66	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6009	Approved
0.6579	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4700	Approved
0.6574	Remote Similarity	NPD6404	Discontinued
0.6571	Remote Similarity	NPD5282	Discontinued
0.6555	Remote Similarity	NPD6319	Approved
0.6545	Remote Similarity	NPD6052	Approved
0.6535	Remote Similarity	NPD5690	Phase 2
0.6535	Remote Similarity	NPD5280	Approved
0.6535	Remote Similarity	NPD4694	Approved
0.6522	Remote Similarity	NPD4691	Approved
0.6518	Remote Similarity	NPD6614	Approved
0.6518	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5344	Discontinued
0.6508	Remote Similarity	NPD6845	Suspended
0.6505	Remote Similarity	NPD4753	Phase 2
0.65	Remote Similarity	NPD8513	Phase 3
0.65	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8515	Approved
0.65	Remote Similarity	NPD8517	Approved
0.65	Remote Similarity	NPD8516	Approved
0.6491	Remote Similarity	NPD6371	Approved
0.6489	Remote Similarity	NPD5733	Approved
0.6475	Remote Similarity	NPD7492	Approved
0.6466	Remote Similarity	NPD6858	Approved
0.6466	Remote Similarity	NPD7094	Approved
0.6465	Remote Similarity	NPD4223	Phase 3
0.6465	Remote Similarity	NPD4221	Approved
0.646	Remote Similarity	NPD4729	Approved
0.646	Remote Similarity	NPD4730	Approved
0.6452	Remote Similarity	NPD5276	Approved
0.6449	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7732	Phase 3
0.6436	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD1696	Phase 3
0.6429	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7507	Approved
0.6423	Remote Similarity	NPD6616	Approved
0.6417	Remote Similarity	NPD6054	Approved
0.6413	Remote Similarity	NPD4137	Phase 3
0.64	Remote Similarity	NPD5362	Discontinued
0.64	Remote Similarity	NPD7154	Phase 3
0.6396	Remote Similarity	NPD4754	Approved
0.6393	Remote Similarity	NPD7604	Phase 2
0.6392	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6412	Phase 2
0.6371	Remote Similarity	NPD7078	Approved
0.6364	Remote Similarity	NPD6016	Approved
0.6364	Remote Similarity	NPD6015	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