NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	361.978
LogP:	2.615
LogD:	1.43
LogS:	-3.972
# Rotatable Bonds:	5
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.824
Synthetic Accessibility Score:	4.428
Fsp3:	0.75
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:	-5.354
MDCK Permeability:	4.2561121517792344e-05
Pgp-inhibitor:	0.241
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.32
Plasma Protein Binding (PPB):	88.75676727294922%
Volume Distribution (VD):	0.212
Pgp-substrate:	10.426007270812988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.39
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	4.635
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.504
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.107
Maximum Recommended Daily Dose:	0.291
Skin Sensitization:	0.732
Carcinogencity:	0.516
Eye Corrosion:	0.263
Eye Irritation:	0.404
Respiratory Toxicity:	0.493

Download Data

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

Natural Product: NPC180886

Natural Product ID:	NPC180886
*Common Name:**	(5alpha,8alpha,9R,10beta,13S)-2,7-Dioxocleroda-3-ene-15-oic acid
IUPAC Name:	(3S)-5-[(1R,2S,4aR,8aR)-1,2,4a,5-tetramethyl-3,7-dioxo-2,4,8,8a-tetrahydronaphthalen-1-yl]-3-methylpentanoic acid
Synonyms:
Standard InCHIKey:	WCWSAYZIPUPYKD-SVMSGLSLSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-12(8-18(23)24)6-7-19(4)14(3)16(22)11-20(5)13(2)9-15(21)10-17(19)20/h9,12,14,17H,6-8,10-11H2,1-5H3,(H,23,24)/t12-,14+,17+,19-,20-/m0/s1
SMILES:	C[C@@H]1C(=O)C[C@@]2([C@@H]([C@@]1(C)CC[C@H](C)CC(=O)O)CC(=O)C=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11508272
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19299148]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4.3	ug/ml	PMID[19299148]

☑ 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 NPC180886 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1092
0.2-0.3	5886
0.3-0.4	14645
0.4-0.5	8742
0.5-0.6	6506
0.6-0.7	3974
0.7-0.8	1473
0.8-0.85	151
0.85-0.9	58
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9452	High Similarity	NPC74410
0.9333	High Similarity	NPC278459
0.9315	High Similarity	NPC165711
0.9155	High Similarity	NPC160817
0.9079	High Similarity	NPC471898
0.9079	High Similarity	NPC477372
0.9054	High Similarity	NPC97377
0.8974	High Similarity	NPC96095
0.8961	High Similarity	NPC320514
0.8947	High Similarity	NPC26139
0.8933	High Similarity	NPC321514
0.8904	High Similarity	NPC476046
0.8904	High Similarity	NPC251970
0.8904	High Similarity	NPC241854
0.8846	High Similarity	NPC168188
0.8846	High Similarity	NPC470015
0.8846	High Similarity	NPC49019
0.8846	High Similarity	NPC105803
0.8831	High Similarity	NPC90055
0.8816	High Similarity	NPC477371
0.8816	High Similarity	NPC192329
0.88	High Similarity	NPC472300
0.88	High Similarity	NPC61952
0.8784	High Similarity	NPC279666
0.8784	High Similarity	NPC476795
0.8784	High Similarity	NPC192540
0.8767	High Similarity	NPC130016
0.8767	High Similarity	NPC109576
0.8767	High Similarity	NPC56747
0.8767	High Similarity	NPC180015
0.8718	High Similarity	NPC302661
0.8718	High Similarity	NPC238991
0.8718	High Similarity	NPC133391
0.8701	High Similarity	NPC37038
0.8684	High Similarity	NPC280654
0.8684	High Similarity	NPC198240
0.8684	High Similarity	NPC275494
0.8684	High Similarity	NPC260385
0.8684	High Similarity	NPC189485
0.8684	High Similarity	NPC110094
0.8684	High Similarity	NPC471409
0.8684	High Similarity	NPC179028
0.8667	High Similarity	NPC309399
0.8667	High Similarity	NPC69143
0.8649	High Similarity	NPC183503
0.8649	High Similarity	NPC161923
0.8649	High Similarity	NPC103958
0.8649	High Similarity	NPC301065
0.8649	High Similarity	NPC283908
0.8642	High Similarity	NPC136948
0.8625	High Similarity	NPC474537
0.8625	High Similarity	NPC311702
0.8625	High Similarity	NPC123319
0.8625	High Similarity	NPC29447
0.8625	High Similarity	NPC474680
0.8625	High Similarity	NPC94531
0.8608	High Similarity	NPC477373
0.8608	High Similarity	NPC97913
0.8608	High Similarity	NPC102197
0.859	High Similarity	NPC162632
0.859	High Similarity	NPC267691
0.859	High Similarity	NPC472684
0.859	High Similarity	NPC189237
0.859	High Similarity	NPC38350
0.859	High Similarity	NPC116797
0.859	High Similarity	NPC263272
0.859	High Similarity	NPC201912
0.859	High Similarity	NPC55869
0.859	High Similarity	NPC147066
0.859	High Similarity	NPC274050
0.859	High Similarity	NPC327002
0.859	High Similarity	NPC44963
0.8571	High Similarity	NPC327674
0.8571	High Similarity	NPC199595
0.8571	High Similarity	NPC231431
0.8553	High Similarity	NPC257666
0.8553	High Similarity	NPC471897
0.8553	High Similarity	NPC266193
0.8553	High Similarity	NPC107039
0.8553	High Similarity	NPC471899
0.8537	High Similarity	NPC48107
0.8537	High Similarity	NPC72397
0.8533	High Similarity	NPC476346
0.8514	High Similarity	NPC35656
0.85	High Similarity	NPC472865
0.85	High Similarity	NPC164577
0.8481	Intermediate Similarity	NPC260956
0.8481	Intermediate Similarity	NPC69101
0.8481	Intermediate Similarity	NPC251779
0.8462	Intermediate Similarity	NPC2482
0.8462	Intermediate Similarity	NPC108955
0.8462	Intermediate Similarity	NPC476809
0.8462	Intermediate Similarity	NPC104545
0.8442	Intermediate Similarity	NPC59436
0.8434	Intermediate Similarity	NPC262043
0.8434	Intermediate Similarity	NPC36668
0.8434	Intermediate Similarity	NPC118011
0.8434	Intermediate Similarity	NPC5509
0.8434	Intermediate Similarity	NPC477973
0.8421	Intermediate Similarity	NPC263582
0.8421	Intermediate Similarity	NPC89294
0.8415	Intermediate Similarity	NPC476409
0.84	Intermediate Similarity	NPC237591
0.84	Intermediate Similarity	NPC3753
0.8395	Intermediate Similarity	NPC11711
0.8395	Intermediate Similarity	NPC142649
0.8378	Intermediate Similarity	NPC133253
0.8375	Intermediate Similarity	NPC83569
0.8375	Intermediate Similarity	NPC70834
0.8375	Intermediate Similarity	NPC69279
0.8354	Intermediate Similarity	NPC226068
0.8354	Intermediate Similarity	NPC40228
0.8354	Intermediate Similarity	NPC473420
0.8354	Intermediate Similarity	NPC221647
0.8354	Intermediate Similarity	NPC121984
0.8354	Intermediate Similarity	NPC142244
0.8333	Intermediate Similarity	NPC16394
0.8313	Intermediate Similarity	NPC473229
0.8312	Intermediate Similarity	NPC197659
0.8293	Intermediate Similarity	NPC472869
0.8289	Intermediate Similarity	NPC476844
0.8272	Intermediate Similarity	NPC248758
0.8272	Intermediate Similarity	NPC19849
0.8272	Intermediate Similarity	NPC209882
0.8272	Intermediate Similarity	NPC472864
0.8272	Intermediate Similarity	NPC156981
0.8267	Intermediate Similarity	NPC472813
0.825	Intermediate Similarity	NPC193347
0.825	Intermediate Similarity	NPC327969
0.825	Intermediate Similarity	NPC321289
0.825	Intermediate Similarity	NPC103486
0.8235	Intermediate Similarity	NPC233455
0.8235	Intermediate Similarity	NPC230064
0.8235	Intermediate Similarity	NPC158030
0.8235	Intermediate Similarity	NPC145067
0.8235	Intermediate Similarity	NPC204341
0.8235	Intermediate Similarity	NPC65120
0.8235	Intermediate Similarity	NPC4036
0.8228	Intermediate Similarity	NPC472478
0.8228	Intermediate Similarity	NPC477057
0.8219	Intermediate Similarity	NPC290445
0.8219	Intermediate Similarity	NPC36616
0.8214	Intermediate Similarity	NPC112454
0.8205	Intermediate Similarity	NPC62336
0.8205	Intermediate Similarity	NPC30321
0.8193	Intermediate Similarity	NPC173089
0.8193	Intermediate Similarity	NPC158141
0.8193	Intermediate Similarity	NPC181327
0.8193	Intermediate Similarity	NPC96496
0.8182	Intermediate Similarity	NPC40353
0.8182	Intermediate Similarity	NPC76966
0.8182	Intermediate Similarity	NPC470525
0.8182	Intermediate Similarity	NPC7629
0.8182	Intermediate Similarity	NPC92080
0.8182	Intermediate Similarity	NPC151622
0.8182	Intermediate Similarity	NPC186554
0.8182	Intermediate Similarity	NPC472305
0.8171	Intermediate Similarity	NPC189311
0.8171	Intermediate Similarity	NPC263997
0.8171	Intermediate Similarity	NPC8518
0.8171	Intermediate Similarity	NPC132228
0.8171	Intermediate Similarity	NPC473038
0.8171	Intermediate Similarity	NPC6185
0.8171	Intermediate Similarity	NPC241512
0.8169	Intermediate Similarity	NPC234767
0.8158	Intermediate Similarity	NPC213223
0.8148	Intermediate Similarity	NPC53733
0.8148	Intermediate Similarity	NPC200752
0.814	Intermediate Similarity	NPC263780
0.814	Intermediate Similarity	NPC295643
0.814	Intermediate Similarity	NPC272075
0.814	Intermediate Similarity	NPC214756
0.8133	Intermediate Similarity	NPC84790
0.8133	Intermediate Similarity	NPC21944
0.8125	Intermediate Similarity	NPC473217
0.8125	Intermediate Similarity	NPC225515
0.8118	Intermediate Similarity	NPC476369
0.8118	Intermediate Similarity	NPC476437
0.8101	Intermediate Similarity	NPC308038
0.8101	Intermediate Similarity	NPC158846
0.8101	Intermediate Similarity	NPC196827
0.8101	Intermediate Similarity	NPC27817
0.8101	Intermediate Similarity	NPC472490
0.8101	Intermediate Similarity	NPC274996
0.8095	Intermediate Similarity	NPC1753
0.8095	Intermediate Similarity	NPC474511
0.8095	Intermediate Similarity	NPC472870
0.8095	Intermediate Similarity	NPC474474
0.8095	Intermediate Similarity	NPC117122
0.8077	Intermediate Similarity	NPC34110
0.8077	Intermediate Similarity	NPC325946
0.8077	Intermediate Similarity	NPC212661
0.8077	Intermediate Similarity	NPC471035
0.8072	Intermediate Similarity	NPC6247
0.8072	Intermediate Similarity	NPC324063
0.8072	Intermediate Similarity	NPC73038
0.8072	Intermediate Similarity	NPC475181
0.8072	Intermediate Similarity	NPC322159
0.8072	Intermediate Similarity	NPC229717
0.8072	Intermediate Similarity	NPC262085

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 NPC180886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1569
0.2-0.3	3940
0.3-0.4	2298
0.4-0.5	687
0.5-0.6	264
0.6-0.7	156
0.7-0.8	81
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
0.8462	Intermediate Similarity	NPD4695	Discontinued
0.825	Intermediate Similarity	NPD4221	Approved
0.825	Intermediate Similarity	NPD4223	Phase 3
0.8235	Intermediate Similarity	NPD5281	Approved
0.8235	Intermediate Similarity	NPD7515	Phase 2
0.8235	Intermediate Similarity	NPD5284	Approved
0.8214	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4197	Approved
0.8049	Intermediate Similarity	NPD3665	Phase 1
0.8049	Intermediate Similarity	NPD3133	Approved
0.8049	Intermediate Similarity	NPD3666	Approved
0.8046	Intermediate Similarity	NPD7748	Approved
0.7975	Intermediate Similarity	NPD3617	Approved
0.7955	Intermediate Similarity	NPD5695	Phase 3
0.7952	Intermediate Similarity	NPD5329	Approved
0.7882	Intermediate Similarity	NPD6672	Approved
0.7882	Intermediate Similarity	NPD5737	Approved
0.7867	Intermediate Similarity	NPD4137	Phase 3
0.7857	Intermediate Similarity	NPD3618	Phase 1
0.7857	Intermediate Similarity	NPD7146	Approved
0.7857	Intermediate Similarity	NPD4693	Phase 3
0.7857	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4689	Approved
0.7857	Intermediate Similarity	NPD4688	Approved
0.7857	Intermediate Similarity	NPD5280	Approved
0.7857	Intermediate Similarity	NPD5205	Approved
0.7857	Intermediate Similarity	NPD5690	Phase 2
0.7857	Intermediate Similarity	NPD4138	Approved
0.7857	Intermediate Similarity	NPD4694	Approved
0.7857	Intermediate Similarity	NPD6684	Approved
0.7857	Intermediate Similarity	NPD4690	Approved
0.7857	Intermediate Similarity	NPD6409	Approved
0.7857	Intermediate Similarity	NPD4623	Approved
0.7857	Intermediate Similarity	NPD4519	Discontinued
0.7857	Intermediate Similarity	NPD5330	Approved
0.7857	Intermediate Similarity	NPD7521	Approved
0.7857	Intermediate Similarity	NPD7334	Approved
0.7805	Intermediate Similarity	NPD3667	Approved
0.7791	Intermediate Similarity	NPD6904	Approved
0.7791	Intermediate Similarity	NPD4753	Phase 2
0.7791	Intermediate Similarity	NPD6080	Approved
0.7791	Intermediate Similarity	NPD6673	Approved
0.7778	Intermediate Similarity	NPD6083	Phase 2
0.7778	Intermediate Similarity	NPD6084	Phase 2
0.7778	Intermediate Similarity	NPD7902	Approved
0.7765	Intermediate Similarity	NPD3573	Approved
0.7763	Intermediate Similarity	NPD4747	Approved
0.7763	Intermediate Similarity	NPD4691	Approved
0.7727	Intermediate Similarity	NPD6399	Phase 3
0.7703	Intermediate Similarity	NPD7331	Phase 2
0.7701	Intermediate Similarity	NPD5692	Phase 3
0.7692	Intermediate Similarity	NPD5696	Approved
0.7674	Intermediate Similarity	NPD5208	Approved
0.7674	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6903	Approved
0.7667	Intermediate Similarity	NPD7614	Phase 1
0.7647	Intermediate Similarity	NPD5279	Phase 3
0.7619	Intermediate Similarity	NPD4786	Approved
0.7614	Intermediate Similarity	NPD5694	Approved
0.7614	Intermediate Similarity	NPD6050	Approved
0.7614	Intermediate Similarity	NPD5693	Phase 1
0.759	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD5207	Approved
0.7468	Intermediate Similarity	NPD4058	Approved
0.7468	Intermediate Similarity	NPD5733	Approved
0.7468	Intermediate Similarity	NPD4687	Approved
0.7444	Intermediate Similarity	NPD7900	Approved
0.7444	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6098	Approved
0.7439	Intermediate Similarity	NPD4195	Approved
0.7436	Intermediate Similarity	NPD5276	Approved
0.7416	Intermediate Similarity	NPD6079	Approved
0.7412	Intermediate Similarity	NPD3668	Phase 3
0.7363	Intermediate Similarity	NPD4629	Approved
0.7363	Intermediate Similarity	NPD5210	Approved
0.7363	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4202	Approved
0.7333	Intermediate Similarity	NPD7341	Phase 2
0.7303	Intermediate Similarity	NPD4096	Approved
0.7283	Intermediate Similarity	NPD4697	Phase 3
0.7283	Intermediate Similarity	NPD5222	Approved
0.7283	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5221	Approved
0.7273	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4692	Approved
0.7262	Intermediate Similarity	NPD4139	Approved
0.7253	Intermediate Similarity	NPD6001	Approved
0.7222	Intermediate Similarity	NPD287	Approved
0.7216	Intermediate Similarity	NPD6402	Approved
0.7216	Intermediate Similarity	NPD7128	Approved
0.7216	Intermediate Similarity	NPD5739	Approved
0.7216	Intermediate Similarity	NPD6675	Approved
0.7204	Intermediate Similarity	NPD5173	Approved
0.7204	Intermediate Similarity	NPD4755	Approved
0.7174	Intermediate Similarity	NPD5654	Approved
0.7143	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD5133	Approved
0.7143	Intermediate Similarity	NPD5701	Approved
0.7126	Intermediate Similarity	NPD1694	Approved
0.7108	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7732	Phase 3
0.7079	Intermediate Similarity	NPD4518	Approved
0.7071	Intermediate Similarity	NPD6011	Approved
0.7071	Intermediate Similarity	NPD7320	Approved
0.7071	Intermediate Similarity	NPD6881	Approved
0.7071	Intermediate Similarity	NPD6899	Approved
0.7067	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4700	Approved
0.7053	Intermediate Similarity	NPD6404	Discontinued
0.7053	Intermediate Similarity	NPD5286	Approved
0.7053	Intermediate Similarity	NPD5285	Approved
0.7053	Intermediate Similarity	NPD4696	Approved
0.7033	Intermediate Similarity	NPD6411	Approved
0.7021	Intermediate Similarity	NPD5959	Approved
0.7013	Intermediate Similarity	NPD4224	Phase 2
0.7	Intermediate Similarity	NPD6013	Approved
0.7	Intermediate Similarity	NPD6014	Approved
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD6373	Approved
0.7	Intermediate Similarity	NPD6012	Approved
0.6979	Remote Similarity	NPD5223	Approved
0.6947	Remote Similarity	NPD7638	Approved
0.6941	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7290	Approved
0.6931	Remote Similarity	NPD7102	Approved
0.6931	Remote Similarity	NPD6883	Approved
0.6907	Remote Similarity	NPD5225	Approved
0.6907	Remote Similarity	NPD4633	Approved
0.6907	Remote Similarity	NPD5211	Phase 2
0.6907	Remote Similarity	NPD5224	Approved
0.6907	Remote Similarity	NPD5091	Approved
0.6907	Remote Similarity	NPD5226	Approved
0.6897	Remote Similarity	NPD4788	Approved
0.6875	Remote Similarity	NPD7640	Approved
0.6875	Remote Similarity	NPD7639	Approved
0.6863	Remote Similarity	NPD6649	Approved
0.6863	Remote Similarity	NPD6847	Approved
0.6863	Remote Similarity	NPD6650	Approved
0.6863	Remote Similarity	NPD8130	Phase 1
0.6863	Remote Similarity	NPD6617	Approved
0.6863	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6869	Approved
0.6837	Remote Similarity	NPD5174	Approved
0.6837	Remote Similarity	NPD6052	Approved
0.6837	Remote Similarity	NPD4754	Approved
0.6837	Remote Similarity	NPD5175	Approved
0.6813	Remote Similarity	NPD6101	Approved
0.6813	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6412	Phase 2
0.6796	Remote Similarity	NPD8297	Approved
0.6796	Remote Similarity	NPD6882	Approved
0.679	Remote Similarity	NPD6081	Approved
0.679	Remote Similarity	NPD4243	Approved
0.6786	Remote Similarity	NPD4756	Discovery
0.6768	Remote Similarity	NPD5141	Approved
0.6761	Remote Similarity	NPD3172	Approved
0.6747	Remote Similarity	NPD8039	Approved
0.6744	Remote Similarity	NPD5368	Approved
0.6742	Remote Similarity	NPD5363	Approved
0.6739	Remote Similarity	NPD5785	Approved
0.6731	Remote Similarity	NPD4632	Approved
0.6711	Remote Similarity	NPD4194	Approved
0.6711	Remote Similarity	NPD4192	Approved
0.6711	Remote Similarity	NPD4193	Approved
0.6711	Remote Similarity	NPD4191	Approved
0.6705	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4767	Approved
0.67	Remote Similarity	NPD4768	Approved
0.67	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3196	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD3195	Phase 2
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD3194	Approved
0.6667	Remote Similarity	NPD8028	Phase 2
0.6667	Remote Similarity	NPD4266	Approved
0.6634	Remote Similarity	NPD6614	Approved
0.6627	Remote Similarity	NPD4785	Approved
0.6627	Remote Similarity	NPD4784	Approved
0.6604	Remote Similarity	NPD6274	Approved
0.6604	Remote Similarity	NPD6868	Approved
0.6598	Remote Similarity	NPD4225	Approved
0.6596	Remote Similarity	NPD5779	Approved
0.6596	Remote Similarity	NPD5778	Approved
0.6591	Remote Similarity	NPD4270	Approved
0.6591	Remote Similarity	NPD4269	Approved
0.6591	Remote Similarity	NPD6435	Approved
0.6569	Remote Similarity	NPD4730	Approved
0.6569	Remote Similarity	NPD6686	Approved
0.6569	Remote Similarity	NPD4729	Approved
0.6569	Remote Similarity	NPD5168	Approved
0.6569	Remote Similarity	NPD5128	Approved
0.6556	Remote Similarity	NPD1696	Phase 3
0.6548	Remote Similarity	NPD5275	Approved
0.6548	Remote Similarity	NPD6942	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