NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	402.24
Volume:	434.68
LogP:	3.406
LogD:	3.035
LogS:	-3.967
# Rotatable Bonds:	10
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	5.199
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.761
MDCK Permeability:	1.813538619899191e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.032
20% Bioavailability (F20%):	0.128
30% Bioavailability (F30%):	0.235

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	69.97651672363281%
Volume Distribution (VD):	1.814
Pgp-substrate:	39.960853576660156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.289
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.835
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	7.477
Half-life (T1/2):	0.596

ADMET: Toxicity

hERG Blockers:	0.171
Human Hepatotoxicity (H-HT):	0.604
Drug-inuced Liver Injury (DILI):	0.253
AMES Toxicity:	0.631
Rat Oral Acute Toxicity:	0.844
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.976
Carcinogencity:	0.706
Eye Corrosion:	0.298
Eye Irritation:	0.052
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC476802

Natural Product ID:	NPC476802
*Common Name:**	Caseanigrescen D2
IUPAC Name:	[(2R,4aS,5S,7R,8R,8aS)-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-(3-methylidenepent-4-enyl)-1,2,5,6,7,8a-hexahydronaphthalen-2-yl] butanoate
Synonyms:	Caseanigrescen D2
Standard InCHIKey:	LJKLFXDBDBCJPX-UYLBCASOSA-N
Standard InCHI:	InChI=1S/C24H34O5/c1-6-8-22(28)29-19-12-18(14-25)24(15-26)20(13-19)23(5,10-9-16(3)7-2)17(4)11-21(24)27/h7,12,14-15,17,19-21,27H,2-3,6,8-11,13H2,1,4-5H3/t17-,19+,20+,21+,23-,24+/m1/s1
SMILES:	CCCC(=O)O[C@@H]1C[C@H]2[C@]([C@@H](C[C@@H]([C@]2(C(=C1)C=O)C=O)O)C)(C)CCC(=C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16109796
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
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17315961]
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	n.a.	flower	n.a.	PMID[17315961]
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	leaves and flowers	Zahamena region of Madagascar, Toamasina, 3 km northeast of Nosivola (1741'01?S, 4838'28?)	2001-NOV	PMID[17315961]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1500	nM	PMID[17315961]

☑ 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 NPC476802 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	221
0.1-0.2	1206
0.2-0.3	3693
0.3-0.4	6655
0.4-0.5	12552
0.5-0.6	9581
0.6-0.7	6508
0.7-0.8	2180
0.8-0.85	95
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC89171
0.9612	High Similarity	NPC476801
0.95	High Similarity	NPC470297
0.8704	High Similarity	NPC277769
0.8679	High Similarity	NPC189075
0.8679	High Similarity	NPC275539
0.8667	High Similarity	NPC1679
0.8667	High Similarity	NPC469607
0.8654	High Similarity	NPC95585
0.8654	High Similarity	NPC282233
0.8641	High Similarity	NPC471412
0.8627	High Similarity	NPC23364
0.8598	High Similarity	NPC474243
0.8585	High Similarity	NPC110496
0.8559	High Similarity	NPC474518
0.8545	High Similarity	NPC238667
0.8544	High Similarity	NPC471413
0.8532	High Similarity	NPC4573
0.8532	High Similarity	NPC90952
0.8515	High Similarity	NPC183012
0.8476	Intermediate Similarity	NPC95899
0.8476	Intermediate Similarity	NPC120321
0.8416	Intermediate Similarity	NPC470697
0.8416	Intermediate Similarity	NPC250075
0.8396	Intermediate Similarity	NPC118911
0.8393	Intermediate Similarity	NPC134430
0.8393	Intermediate Similarity	NPC476959
0.8381	Intermediate Similarity	NPC273005
0.8381	Intermediate Similarity	NPC31058
0.8381	Intermediate Similarity	NPC469606
0.8381	Intermediate Similarity	NPC162973
0.8365	Intermediate Similarity	NPC476299
0.8365	Intermediate Similarity	NPC474012
0.8365	Intermediate Similarity	NPC174314
0.8364	Intermediate Similarity	NPC12046
0.8364	Intermediate Similarity	NPC194951
0.8364	Intermediate Similarity	NPC269530
0.8333	Intermediate Similarity	NPC476962
0.8333	Intermediate Similarity	NPC476479
0.8319	Intermediate Similarity	NPC284707
0.8302	Intermediate Similarity	NPC254202
0.8288	Intermediate Similarity	NPC25909
0.8288	Intermediate Similarity	NPC471204
0.8288	Intermediate Similarity	NPC157441
0.8288	Intermediate Similarity	NPC469463
0.8288	Intermediate Similarity	NPC56448
0.8288	Intermediate Similarity	NPC469454
0.8288	Intermediate Similarity	NPC469496
0.8286	Intermediate Similarity	NPC111292
0.8283	Intermediate Similarity	NPC473229
0.8269	Intermediate Similarity	NPC316598
0.8269	Intermediate Similarity	NPC216478
0.8252	Intermediate Similarity	NPC29952
0.8252	Intermediate Similarity	NPC202833
0.8246	Intermediate Similarity	NPC476960
0.8246	Intermediate Similarity	NPC473636
0.8246	Intermediate Similarity	NPC77689
0.8241	Intermediate Similarity	NPC179380
0.823	Intermediate Similarity	NPC469684
0.823	Intermediate Similarity	NPC53396
0.823	Intermediate Similarity	NPC475809
0.823	Intermediate Similarity	NPC98249
0.8224	Intermediate Similarity	NPC96268
0.8218	Intermediate Similarity	NPC477574
0.8214	Intermediate Similarity	NPC470953
0.8208	Intermediate Similarity	NPC164551
0.8208	Intermediate Similarity	NPC476081
0.8208	Intermediate Similarity	NPC137430
0.8198	Intermediate Similarity	NPC69291
0.819	Intermediate Similarity	NPC47024
0.819	Intermediate Similarity	NPC117685
0.819	Intermediate Similarity	NPC54705
0.819	Intermediate Similarity	NPC306856
0.819	Intermediate Similarity	NPC476933
0.8182	Intermediate Similarity	NPC478209
0.8182	Intermediate Similarity	NPC5103
0.8174	Intermediate Similarity	NPC476961
0.8173	Intermediate Similarity	NPC474343
0.8165	Intermediate Similarity	NPC306265
0.8165	Intermediate Similarity	NPC151393
0.8165	Intermediate Similarity	NPC322903
0.8158	Intermediate Similarity	NPC21326
0.8148	Intermediate Similarity	NPC478208
0.8142	Intermediate Similarity	NPC469794
0.8142	Intermediate Similarity	NPC476963
0.8142	Intermediate Similarity	NPC72772
0.8131	Intermediate Similarity	NPC8196
0.8131	Intermediate Similarity	NPC478057
0.8131	Intermediate Similarity	NPC156681
0.8131	Intermediate Similarity	NPC159533
0.8131	Intermediate Similarity	NPC99266
0.8131	Intermediate Similarity	NPC159442
0.8125	Intermediate Similarity	NPC159333
0.8125	Intermediate Similarity	NPC472926
0.812	Intermediate Similarity	NPC55602
0.812	Intermediate Similarity	NPC469789
0.812	Intermediate Similarity	NPC11895
0.8119	Intermediate Similarity	NPC158488
0.8113	Intermediate Similarity	NPC224720
0.8113	Intermediate Similarity	NPC476240
0.8113	Intermediate Similarity	NPC242666
0.8113	Intermediate Similarity	NPC476223
0.8113	Intermediate Similarity	NPC472637
0.8113	Intermediate Similarity	NPC303559
0.8108	Intermediate Similarity	NPC179798
0.8108	Intermediate Similarity	NPC304180
0.8108	Intermediate Similarity	NPC474315
0.8108	Intermediate Similarity	NPC188738
0.8095	Intermediate Similarity	NPC57079
0.8095	Intermediate Similarity	NPC478056
0.8095	Intermediate Similarity	NPC108368
0.8095	Intermediate Similarity	NPC476807
0.8095	Intermediate Similarity	NPC476806
0.8087	Intermediate Similarity	NPC473839
0.8087	Intermediate Similarity	NPC211093
0.8077	Intermediate Similarity	NPC242848
0.8077	Intermediate Similarity	NPC134072
0.8077	Intermediate Similarity	NPC61369
0.8077	Intermediate Similarity	NPC234993
0.8077	Intermediate Similarity	NPC469545
0.8077	Intermediate Similarity	NPC5532
0.8073	Intermediate Similarity	NPC78966
0.8073	Intermediate Similarity	NPC143609
0.8073	Intermediate Similarity	NPC133422
0.8073	Intermediate Similarity	NPC472925
0.8073	Intermediate Similarity	NPC284732
0.807	Intermediate Similarity	NPC239273
0.807	Intermediate Similarity	NPC284068
0.807	Intermediate Similarity	NPC472927
0.8058	Intermediate Similarity	NPC477130
0.8058	Intermediate Similarity	NPC477129
0.8058	Intermediate Similarity	NPC57117
0.8058	Intermediate Similarity	NPC269729
0.8056	Intermediate Similarity	NPC189616
0.8056	Intermediate Similarity	NPC146731
0.8056	Intermediate Similarity	NPC239162
0.8056	Intermediate Similarity	NPC296950
0.8051	Intermediate Similarity	NPC172154
0.8051	Intermediate Similarity	NPC8369
0.8051	Intermediate Similarity	NPC81736
0.8039	Intermediate Similarity	NPC233345
0.8039	Intermediate Similarity	NPC186363
0.8039	Intermediate Similarity	NPC473944
0.8037	Intermediate Similarity	NPC155332
0.8037	Intermediate Similarity	NPC136289
0.8037	Intermediate Similarity	NPC114540
0.8037	Intermediate Similarity	NPC165250
0.8037	Intermediate Similarity	NPC32577
0.8037	Intermediate Similarity	NPC235369
0.8037	Intermediate Similarity	NPC295791
0.8037	Intermediate Similarity	NPC478156
0.8037	Intermediate Similarity	NPC80781
0.8034	Intermediate Similarity	NPC170538
0.802	Intermediate Similarity	NPC168131
0.8019	Intermediate Similarity	NPC475385
0.8019	Intermediate Similarity	NPC474718
0.8019	Intermediate Similarity	NPC471041
0.8019	Intermediate Similarity	NPC35751
0.8019	Intermediate Similarity	NPC475392
0.8019	Intermediate Similarity	NPC472972
0.8019	Intermediate Similarity	NPC475202
0.8019	Intermediate Similarity	NPC476274
0.8018	Intermediate Similarity	NPC286880
0.8018	Intermediate Similarity	NPC470496
0.8018	Intermediate Similarity	NPC179642
0.8017	Intermediate Similarity	NPC184555
0.8	Intermediate Similarity	NPC473483
0.8	Intermediate Similarity	NPC287668
0.8	Intermediate Similarity	NPC285513
0.8	Intermediate Similarity	NPC254496
0.8	Intermediate Similarity	NPC91695
0.8	Intermediate Similarity	NPC37628
0.8	Intermediate Similarity	NPC73911
0.8	Intermediate Similarity	NPC70145
0.7983	Intermediate Similarity	NPC293112
0.7982	Intermediate Similarity	NPC111952
0.7982	Intermediate Similarity	NPC123726
0.7982	Intermediate Similarity	NPC284365
0.7982	Intermediate Similarity	NPC102352
0.7982	Intermediate Similarity	NPC196931
0.7982	Intermediate Similarity	NPC252296
0.7982	Intermediate Similarity	NPC34768
0.7981	Intermediate Similarity	NPC471786
0.7981	Intermediate Similarity	NPC209355
0.7981	Intermediate Similarity	NPC274417
0.7981	Intermediate Similarity	NPC37603
0.7966	Intermediate Similarity	NPC204812
0.7966	Intermediate Similarity	NPC120724
0.7965	Intermediate Similarity	NPC478212
0.7965	Intermediate Similarity	NPC321496
0.7965	Intermediate Similarity	NPC122056
0.7963	Intermediate Similarity	NPC476848
0.7963	Intermediate Similarity	NPC275583
0.7963	Intermediate Similarity	NPC36688
0.7963	Intermediate Similarity	NPC476889
0.7963	Intermediate Similarity	NPC176883
0.7961	Intermediate Similarity	NPC475657
0.7961	Intermediate Similarity	NPC115021
0.7961	Intermediate Similarity	NPC139692
0.7949	Intermediate Similarity	NPC67569

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 NPC476802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1508
0.2-0.3	3310
0.3-0.4	2533
0.4-0.5	1050
0.5-0.6	334
0.6-0.7	192
0.7-0.8	25
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
0.7961	Intermediate Similarity	NPD5779	Approved
0.7961	Intermediate Similarity	NPD5778	Approved
0.7925	Intermediate Similarity	NPD7638	Approved
0.785	Intermediate Similarity	NPD7640	Approved
0.785	Intermediate Similarity	NPD7639	Approved
0.7759	Intermediate Similarity	NPD7115	Discovery
0.7757	Intermediate Similarity	NPD4225	Approved
0.7692	Intermediate Similarity	NPD6411	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD6101	Approved
0.75	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD6650	Approved
0.7478	Intermediate Similarity	NPD6649	Approved
0.7451	Intermediate Similarity	NPD1694	Approved
0.7407	Intermediate Similarity	NPD4697	Phase 3
0.7383	Intermediate Similarity	NPD7748	Approved
0.7368	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6899	Approved
0.7368	Intermediate Similarity	NPD6881	Approved
0.736	Intermediate Similarity	NPD7319	Approved
0.7358	Intermediate Similarity	NPD6079	Approved
0.7358	Intermediate Similarity	NPD7515	Phase 2
0.7315	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6373	Approved
0.7304	Intermediate Similarity	NPD6372	Approved
0.729	Intermediate Similarity	NPD6399	Phase 3
0.7281	Intermediate Similarity	NPD5697	Approved
0.7273	Intermediate Similarity	NPD6319	Approved
0.7264	Intermediate Similarity	NPD5785	Approved
0.7258	Intermediate Similarity	NPD7507	Approved
0.7241	Intermediate Similarity	NPD7102	Approved
0.7241	Intermediate Similarity	NPD7290	Approved
0.7241	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6883	Approved
0.7232	Intermediate Similarity	NPD7632	Discontinued
0.7222	Intermediate Similarity	NPD7900	Approved
0.7222	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6011	Approved
0.7217	Intermediate Similarity	NPD6686	Approved
0.7203	Intermediate Similarity	NPD4632	Approved
0.7193	Intermediate Similarity	NPD6675	Approved
0.7193	Intermediate Similarity	NPD6402	Approved
0.7193	Intermediate Similarity	NPD6008	Approved
0.7193	Intermediate Similarity	NPD5739	Approved
0.7193	Intermediate Similarity	NPD7128	Approved
0.7179	Intermediate Similarity	NPD6869	Approved
0.7179	Intermediate Similarity	NPD6847	Approved
0.7179	Intermediate Similarity	NPD8130	Phase 1
0.7179	Intermediate Similarity	NPD6617	Approved
0.7177	Intermediate Similarity	NPD7492	Approved
0.717	Intermediate Similarity	NPD5328	Approved
0.7157	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6012	Approved
0.7155	Intermediate Similarity	NPD6013	Approved
0.7155	Intermediate Similarity	NPD6014	Approved
0.7155	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3573	Approved
0.7131	Intermediate Similarity	NPD6054	Approved
0.712	Intermediate Similarity	NPD6616	Approved
0.7119	Intermediate Similarity	NPD6053	Discontinued
0.7119	Intermediate Similarity	NPD8297	Approved
0.7119	Intermediate Similarity	NPD6882	Approved
0.7097	Intermediate Similarity	NPD8328	Phase 3
0.7091	Intermediate Similarity	NPD5222	Approved
0.7091	Intermediate Similarity	NPD5221	Approved
0.7091	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8513	Phase 3
0.7073	Intermediate Similarity	NPD8516	Approved
0.7073	Intermediate Similarity	NPD8515	Approved
0.7073	Intermediate Similarity	NPD8517	Approved
0.7069	Intermediate Similarity	NPD7320	Approved
0.7063	Intermediate Similarity	NPD7078	Approved
0.7048	Intermediate Similarity	NPD3618	Phase 1
0.7037	Intermediate Similarity	NPD7983	Approved
0.7037	Intermediate Similarity	NPD7637	Suspended
0.7027	Intermediate Similarity	NPD5173	Approved
0.7025	Intermediate Similarity	NPD6009	Approved
0.7016	Intermediate Similarity	NPD6370	Approved
0.7008	Intermediate Similarity	NPD7736	Approved
0.6991	Remote Similarity	NPD5344	Discontinued
0.6983	Remote Similarity	NPD5701	Approved
0.6983	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7260	Phase 2
0.6964	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7604	Phase 2
0.6949	Remote Similarity	NPD6371	Approved
0.6949	Remote Similarity	NPD4634	Approved
0.6944	Remote Similarity	NPD46	Approved
0.6944	Remote Similarity	NPD6698	Approved
0.6942	Remote Similarity	NPD6868	Approved
0.6935	Remote Similarity	NPD6016	Approved
0.6935	Remote Similarity	NPD6015	Approved
0.6935	Remote Similarity	NPD5983	Phase 2
0.693	Remote Similarity	NPD5211	Phase 2
0.6903	Remote Similarity	NPD4696	Approved
0.6903	Remote Similarity	NPD5285	Approved
0.6903	Remote Similarity	NPD6648	Approved
0.6903	Remote Similarity	NPD5286	Approved
0.6891	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5786	Approved
0.6885	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5988	Approved
0.6855	Remote Similarity	NPD6059	Approved
0.685	Remote Similarity	NPD6336	Discontinued
0.6842	Remote Similarity	NPD5223	Approved
0.6829	Remote Similarity	NPD6335	Approved
0.681	Remote Similarity	NPD5141	Approved
0.6797	Remote Similarity	NPD8074	Phase 3
0.6797	Remote Similarity	NPD8293	Discontinued
0.6792	Remote Similarity	NPD5363	Approved
0.6789	Remote Similarity	NPD7838	Discovery
0.6786	Remote Similarity	NPD7839	Suspended
0.6783	Remote Similarity	NPD5224	Approved
0.6783	Remote Similarity	NPD5226	Approved
0.6783	Remote Similarity	NPD4633	Approved
0.6783	Remote Similarity	NPD5225	Approved
0.6774	Remote Similarity	NPD7101	Approved
0.6774	Remote Similarity	NPD7100	Approved
0.6748	Remote Similarity	NPD6317	Approved
0.6729	Remote Similarity	NPD6684	Approved
0.6729	Remote Similarity	NPD7334	Approved
0.6729	Remote Similarity	NPD6409	Approved
0.6729	Remote Similarity	NPD7521	Approved
0.6729	Remote Similarity	NPD5330	Approved
0.6729	Remote Similarity	NPD7146	Approved
0.6729	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8034	Phase 2
0.6727	Remote Similarity	NPD8035	Phase 2
0.6726	Remote Similarity	NPD6084	Phase 2
0.6726	Remote Similarity	NPD6083	Phase 2
0.6726	Remote Similarity	NPD4755	Approved
0.6724	Remote Similarity	NPD5174	Approved
0.6724	Remote Similarity	NPD5175	Approved
0.6723	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4786	Approved
0.6695	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6313	Approved
0.6694	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6634	Remote Similarity	NPD8039	Approved
0.6609	Remote Similarity	NPD4700	Approved
0.6607	Remote Similarity	NPD5282	Discontinued
0.6606	Remote Similarity	NPD6672	Approved
0.6606	Remote Similarity	NPD6903	Approved
0.6606	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5737	Approved
0.6577	Remote Similarity	NPD5281	Approved
0.6577	Remote Similarity	NPD5284	Approved
0.6555	Remote Similarity	NPD6412	Phase 2
0.6549	Remote Similarity	NPD5695	Phase 3
0.6549	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD3665	Phase 1
0.6542	Remote Similarity	NPD3133	Approved
0.6542	Remote Similarity	NPD3666	Approved
0.6541	Remote Similarity	NPD6845	Suspended
0.6522	Remote Similarity	NPD5696	Approved
0.6518	Remote Similarity	NPD4202	Approved
0.6509	Remote Similarity	NPD5209	Approved
0.6509	Remote Similarity	NPD4270	Approved
0.6509	Remote Similarity	NPD4269	Approved
0.65	Remote Similarity	NPD4730	Approved
0.65	Remote Similarity	NPD5168	Approved
0.65	Remote Similarity	NPD4729	Approved
0.6489	Remote Similarity	NPD6033	Approved
0.6481	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4695	Discontinued
0.6476	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4754	Approved
0.6429	Remote Similarity	NPD7328	Approved
0.6429	Remote Similarity	NPD7327	Approved
0.6429	Remote Similarity	NPD5693	Phase 1
0.6423	Remote Similarity	NPD6334	Approved
0.6423	Remote Similarity	NPD6333	Approved
0.6422	Remote Similarity	NPD5279	Phase 3
0.6415	Remote Similarity	NPD5369	Approved
0.6406	Remote Similarity	NPD6909	Approved
0.6406	Remote Similarity	NPD6908	Approved
0.6406	Remote Similarity	NPD8033	Approved
0.6404	Remote Similarity	NPD5210	Approved
0.6404	Remote Similarity	NPD4629	Approved
0.6393	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5249	Phase 3
0.6393	Remote Similarity	NPD5251	Approved
0.6393	Remote Similarity	NPD5169	Approved
0.6393	Remote Similarity	NPD5248	Approved
0.6393	Remote Similarity	NPD5250	Approved
0.6393	Remote Similarity	NPD5135	Approved
0.6393	Remote Similarity	NPD5247	Approved
0.6389	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7516	Approved
0.6364	Remote Similarity	NPD5128	Approved
0.635	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5216	Approved
0.6341	Remote Similarity	NPD5217	Approved
0.6341	Remote Similarity	NPD5127	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