NPASS Compound

Structure

CID35000 OpenBabel06191715362D 32 36 0 0 1 0 0 0 0 0999 V2000 6.0287 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5422 -2.0763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -3.4054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 -4.3784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1087 -3.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -3.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4213 -4.4248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2131 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4120 -3.2013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5036 -2.8526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -2.4324 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2131 -2.4324 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0557 -3.8919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0557 -2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 -2.9189 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5279 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8983 -4.3784 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7719 -0.3807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3611 -4.1729 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 4 24 1 0 0 0 0 6 10 1 0 0 0 0 6 16 1 0 0 0 0 7 9 2 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 31 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 31 1 0 0 0 0 15 26 1 0 0 0 0 16 23 1 1 0 0 0 16 25 1 0 0 0 0 17 22 1 0 0 0 0 17 23 1 1 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 27 2 0 0 0 0 20 25 1 6 0 0 0 20 28 1 0 0 0 0 21 29 2 0 0 0 0 21 32 1 0 0 0 0 23 3 1 1 0 0 0 24 26 1 1 0 0 0 25 5 1 1 0 0 0 26 30 1 1 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.22
Volume:	452.392
LogP:	2.427
LogD:	1.635
LogS:	-4.501
# Rotatable Bonds:	1
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	5.175
Fsp3:	0.615
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.254
MDCK Permeability:	2.872607365134172e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.868
30% Bioavailability (F30%):	0.872

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.659
Plasma Protein Binding (PPB):	90.02200317382812%
Volume Distribution (VD):	2.095
Pgp-substrate:	9.096412658691406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.172
CYP2C19-inhibitor:	0.263
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.578
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.85

ADMET: Excretion

Clearance (CL):	2.995
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.313
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.317
Carcinogencity:	0.237
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC35000

Natural Product ID:	NPC35000
*Common Name:**	7-Deacetyl-17-Epinimolicinol
IUPAC Name:	(1R,4bR,5R,6aR,10aR,10bR,12aR)-1-(furan-3-yl)-1,5-dihydroxy-4b,7,7,10a,12a-pentamethyl-5,6,6a,10b,11,12-hexahydronaphtho[2,1-f]isochromene-3,8-dione
Synonyms:
Standard InCHIKey:	KBHQRXUIHKRZTP-GRSHXKAVSA-N
Standard InCHI:	InChI=1S/C26H32O6/c1-22(2)17-12-20(28)25(5)16(23(17,3)9-7-19(22)27)6-10-24(4)18(25)13-21(29)32-26(24,30)15-8-11-31-14-15/h7-9,11,13-14,16-17,20,28,30H,6,10,12H2,1-5H3/t16-,17+,20-,23-,24-,25-,26+/m1/s1
SMILES:	O=C1C=C2[C@]3(C)[C@H](O)C[C@@H]4[C@]([C@H]3CC[C@]2([C@](O1)(O)c1ccoc1)C)(C)C=CC(=O)C4(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774407
PubChem CID:	52952113
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	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	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	20000.0	nM	PMID[524124]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[524124]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[524124]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[524124]

☑ 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 NPC35000 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	330
0.1-0.2	1280
0.2-0.3	2893
0.3-0.4	5071
0.4-0.5	9511
0.5-0.6	10405
0.6-0.7	8537
0.7-0.8	4183
0.8-0.85	265
0.85-0.9	192
0.9-0.95	27
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC30222
0.9536	High Similarity	NPC307383
0.953	High Similarity	NPC178932
0.9467	High Similarity	NPC469336
0.9463	High Similarity	NPC469503
0.9272	High Similarity	NPC282445
0.9226	High Similarity	NPC198047
0.9216	High Similarity	NPC249021
0.92	High Similarity	NPC469335
0.92	High Similarity	NPC159927
0.9184	High Similarity	NPC476944
0.9167	High Similarity	NPC470182
0.9161	High Similarity	NPC211777
0.9161	High Similarity	NPC5079
0.9161	High Similarity	NPC69028
0.9161	High Similarity	NPC207978
0.9156	High Similarity	NPC474611
0.9133	High Similarity	NPC472654
0.9133	High Similarity	NPC195325
0.9128	High Similarity	NPC250228
0.9122	High Similarity	NPC41182
0.9103	High Similarity	NPC51568
0.9103	High Similarity	NPC234660
0.9091	High Similarity	NPC472772
0.9073	High Similarity	NPC196864
0.9073	High Similarity	NPC477404
0.9045	High Similarity	NPC470940
0.9045	High Similarity	NPC276551
0.9038	High Similarity	NPC82851
0.9038	High Similarity	NPC329938
0.9038	High Similarity	NPC200782
0.9032	High Similarity	NPC262872
0.902	High Similarity	NPC57998
0.9	High Similarity	NPC471174
0.8987	High Similarity	NPC97574
0.8987	High Similarity	NPC470875
0.8987	High Similarity	NPC93172
0.8981	High Similarity	NPC419
0.8981	High Similarity	NPC224394
0.8981	High Similarity	NPC663
0.8981	High Similarity	NPC292389
0.8981	High Similarity	NPC477405
0.8981	High Similarity	NPC469338
0.8974	High Similarity	NPC477402
0.8974	High Similarity	NPC335761
0.8968	High Similarity	NPC472776
0.8968	High Similarity	NPC472777
0.8968	High Similarity	NPC472778
0.8961	High Similarity	NPC264943
0.8961	High Similarity	NPC469850
0.8954	High Similarity	NPC75906
0.8954	High Similarity	NPC476939
0.8954	High Similarity	NPC476940
0.8947	High Similarity	NPC476122
0.8933	High Similarity	NPC346
0.8931	High Similarity	NPC100333
0.8924	High Similarity	NPC469849
0.8919	High Similarity	NPC121158
0.8919	High Similarity	NPC62103
0.8919	High Similarity	NPC20578
0.8917	High Similarity	NPC472771
0.891	High Similarity	NPC477403
0.8903	High Similarity	NPC209364
0.8903	High Similarity	NPC469485
0.8875	High Similarity	NPC471397
0.8874	High Similarity	NPC216755
0.8868	High Similarity	NPC472141
0.8861	High Similarity	NPC302369
0.8861	High Similarity	NPC134254
0.8861	High Similarity	NPC472773
0.8861	High Similarity	NPC39986
0.8846	High Similarity	NPC261597
0.8846	High Similarity	NPC472283
0.8846	High Similarity	NPC173544
0.8846	High Similarity	NPC286722
0.8839	High Similarity	NPC214541
0.8839	High Similarity	NPC44675
0.8839	High Similarity	NPC92979
0.8831	High Similarity	NPC33938
0.8831	High Similarity	NPC476201
0.8824	High Similarity	NPC470997
0.882	High Similarity	NPC82602
0.8816	High Similarity	NPC476942
0.8816	High Similarity	NPC476941
0.8812	High Similarity	NPC472282
0.8812	High Similarity	NPC173516
0.8805	High Similarity	NPC476858
0.8805	High Similarity	NPC476856
0.8805	High Similarity	NPC476857
0.88	High Similarity	NPC142113
0.88	High Similarity	NPC251865
0.8797	High Similarity	NPC96443
0.8797	High Similarity	NPC263432
0.8797	High Similarity	NPC290400
0.8797	High Similarity	NPC193798
0.879	High Similarity	NPC475295
0.879	High Similarity	NPC475967
0.879	High Similarity	NPC473473
0.8784	High Similarity	NPC67003
0.8782	High Similarity	NPC107646
0.8776	High Similarity	NPC476943
0.8774	High Similarity	NPC114880
0.8765	High Similarity	NPC169299
0.8765	High Similarity	NPC160818
0.8758	High Similarity	NPC211625
0.8758	High Similarity	NPC125182
0.8758	High Similarity	NPC69647
0.8758	High Similarity	NPC296558
0.875	High Similarity	NPC255414
0.875	High Similarity	NPC221809
0.875	High Similarity	NPC476938
0.875	High Similarity	NPC476937
0.875	High Similarity	NPC470941
0.8742	High Similarity	NPC88841
0.8742	High Similarity	NPC288602
0.8742	High Similarity	NPC165218
0.8734	High Similarity	NPC472653
0.8734	High Similarity	NPC25255
0.8733	High Similarity	NPC243577
0.8733	High Similarity	NPC476946
0.8733	High Similarity	NPC223415
0.8726	High Similarity	NPC36655
0.8726	High Similarity	NPC299038
0.8726	High Similarity	NPC45101
0.8718	High Similarity	NPC155939
0.8718	High Similarity	NPC141538
0.8718	High Similarity	NPC296807
0.8718	High Similarity	NPC281258
0.8718	High Similarity	NPC476262
0.8716	High Similarity	NPC90953
0.871	High Similarity	NPC246164
0.871	High Similarity	NPC44577
0.8707	High Similarity	NPC310830
0.8701	High Similarity	NPC212257
0.8701	High Similarity	NPC156189
0.8696	High Similarity	NPC478179
0.8696	High Similarity	NPC476850
0.8696	High Similarity	NPC476861
0.8696	High Similarity	NPC472775
0.8696	High Similarity	NPC472774
0.8696	High Similarity	NPC476853
0.8688	High Similarity	NPC472664
0.8688	High Similarity	NPC123088
0.8679	High Similarity	NPC117986
0.8679	High Similarity	NPC149896
0.8679	High Similarity	NPC188649
0.8671	High Similarity	NPC475226
0.8662	High Similarity	NPC41880
0.8662	High Similarity	NPC60973
0.8649	High Similarity	NPC220094
0.8645	High Similarity	NPC272590
0.8645	High Similarity	NPC18135
0.8642	High Similarity	NPC271235
0.8642	High Similarity	NPC160651
0.8639	High Similarity	NPC46896
0.8636	High Similarity	NPC470998
0.8636	High Similarity	NPC234494
0.8634	High Similarity	NPC475779
0.8634	High Similarity	NPC23387
0.8634	High Similarity	NPC214600
0.8634	High Similarity	NPC478178
0.8625	High Similarity	NPC472139
0.8618	High Similarity	NPC5676
0.8616	High Similarity	NPC475381
0.8609	High Similarity	NPC470741
0.8609	High Similarity	NPC267632
0.8609	High Similarity	NPC103134
0.8608	High Similarity	NPC470118
0.8608	High Similarity	NPC167142
0.8608	High Similarity	NPC304692
0.8608	High Similarity	NPC187149
0.8608	High Similarity	NPC194499
0.86	High Similarity	NPC205765
0.8599	High Similarity	NPC75310
0.859	High Similarity	NPC121615
0.859	High Similarity	NPC147168
0.859	High Similarity	NPC294511
0.8581	High Similarity	NPC186626
0.8581	High Similarity	NPC4764
0.8581	High Similarity	NPC310043
0.8581	High Similarity	NPC476936
0.858	High Similarity	NPC472651
0.8571	High Similarity	NPC158525
0.8571	High Similarity	NPC476860
0.8571	High Similarity	NPC271657
0.8562	High Similarity	NPC472767
0.8562	High Similarity	NPC262198
0.8562	High Similarity	NPC18347
0.8562	High Similarity	NPC62799
0.8562	High Similarity	NPC18986
0.8562	High Similarity	NPC470792
0.8562	High Similarity	NPC470939
0.8553	High Similarity	NPC140952
0.8553	High Similarity	NPC137295
0.8545	High Similarity	NPC471437
0.8544	High Similarity	NPC126723
0.8544	High Similarity	NPC104736
0.8533	High Similarity	NPC56197
0.8528	High Similarity	NPC472652
0.8523	High Similarity	NPC471996

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 NPC35000 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	928
0.2-0.3	1999
0.3-0.4	2550
0.4-0.5	1993
0.5-0.6	1018
0.6-0.7	313
0.7-0.8	62
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8839	High Similarity	NPD5760	Phase 2
0.8839	High Similarity	NPD5761	Phase 2
0.8246	Intermediate Similarity	NPD8434	Phase 2
0.7725	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6765	Approved
0.7644	Intermediate Similarity	NPD6764	Approved
0.7644	Intermediate Similarity	NPD6559	Discontinued
0.761	Intermediate Similarity	NPD4628	Phase 3
0.759	Intermediate Similarity	NPD7819	Suspended
0.7546	Intermediate Similarity	NPD920	Approved
0.7531	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6785	Approved
0.7472	Intermediate Similarity	NPD6784	Approved
0.7456	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3749	Approved
0.7423	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3818	Discontinued
0.7391	Intermediate Similarity	NPD3750	Approved
0.7381	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6273	Approved
0.7365	Intermediate Similarity	NPD7411	Suspended
0.736	Intermediate Similarity	NPD8313	Approved
0.736	Intermediate Similarity	NPD8312	Approved
0.7353	Intermediate Similarity	NPD7075	Discontinued
0.7349	Intermediate Similarity	NPD7458	Discontinued
0.7349	Intermediate Similarity	NPD3226	Approved
0.7337	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8404	Phase 2
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6801	Discontinued
0.7317	Intermediate Similarity	NPD2534	Approved
0.7317	Intermediate Similarity	NPD2533	Approved
0.7317	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2532	Approved
0.7305	Intermediate Similarity	NPD6599	Discontinued
0.7305	Intermediate Similarity	NPD4380	Phase 2
0.7301	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5844	Phase 1
0.7273	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5494	Approved
0.725	Intermediate Similarity	NPD2796	Approved
0.7246	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5402	Approved
0.7222	Intermediate Similarity	NPD2800	Approved
0.7205	Intermediate Similarity	NPD2346	Discontinued
0.7195	Intermediate Similarity	NPD7236	Approved
0.7193	Intermediate Similarity	NPD7768	Phase 2
0.7188	Intermediate Similarity	NPD7033	Discontinued
0.7188	Intermediate Similarity	NPD3748	Approved
0.7188	Intermediate Similarity	NPD2799	Discontinued
0.7182	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7054	Approved
0.716	Intermediate Similarity	NPD1549	Phase 2
0.716	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7135	Intermediate Similarity	NPD7472	Approved
0.7135	Intermediate Similarity	NPD7074	Phase 3
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7126	Intermediate Similarity	NPD6959	Discontinued
0.7126	Intermediate Similarity	NPD5403	Approved
0.7126	Intermediate Similarity	NPD8127	Discontinued
0.7119	Intermediate Similarity	NPD7799	Discontinued
0.7118	Intermediate Similarity	NPD37	Approved
0.7117	Intermediate Similarity	NPD1243	Approved
0.7111	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD919	Approved
0.7108	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2344	Approved
0.7099	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1471	Phase 3
0.7093	Intermediate Similarity	NPD4966	Approved
0.7093	Intermediate Similarity	NPD4967	Phase 2
0.7093	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4965	Approved
0.7081	Intermediate Similarity	NPD1510	Phase 2
0.7065	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7251	Discontinued
0.7048	Intermediate Similarity	NPD6799	Approved
0.7037	Intermediate Similarity	NPD2935	Discontinued
0.7037	Intermediate Similarity	NPD6099	Approved
0.7037	Intermediate Similarity	NPD6100	Approved
0.7035	Intermediate Similarity	NPD3817	Phase 2
0.7025	Intermediate Similarity	NPD3268	Approved
0.7022	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD3751	Discontinued
0.7018	Intermediate Similarity	NPD1934	Approved
0.7017	Intermediate Similarity	NPD7808	Phase 3
0.7006	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD6797	Phase 2
0.6994	Remote Similarity	NPD3882	Suspended
0.6989	Remote Similarity	NPD6232	Discontinued
0.6987	Remote Similarity	NPD2798	Approved
0.6982	Remote Similarity	NPD7239	Suspended
0.6977	Remote Similarity	NPD2801	Approved
0.697	Remote Similarity	NPD7003	Approved
0.6961	Remote Similarity	NPD7685	Pre-registration
0.6957	Remote Similarity	NPD8150	Discontinued
0.6932	Remote Similarity	NPD1247	Approved
0.6928	Remote Similarity	NPD2309	Approved
0.6927	Remote Similarity	NPD7228	Approved
0.6923	Remote Similarity	NPD2797	Approved
0.6918	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6234	Discontinued
0.691	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6166	Phase 2
0.691	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6832	Phase 2
0.6893	Remote Similarity	NPD7229	Phase 3
0.6891	Remote Similarity	NPD7435	Discontinued
0.689	Remote Similarity	NPD6002	Phase 3
0.689	Remote Similarity	NPD6005	Phase 3
0.689	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6004	Phase 3
0.6871	Remote Similarity	NPD4308	Phase 3
0.6852	Remote Similarity	NPD1607	Approved
0.6848	Remote Similarity	NPD8407	Phase 2
0.6845	Remote Similarity	NPD1511	Approved
0.6845	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1608	Approved
0.6836	Remote Similarity	NPD7199	Phase 2
0.6832	Remote Similarity	NPD1240	Approved
0.6831	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3764	Approved
0.6813	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3787	Discontinued
0.6798	Remote Similarity	NPD5711	Approved
0.6798	Remote Similarity	NPD5710	Approved
0.6796	Remote Similarity	NPD7286	Phase 2
0.6782	Remote Similarity	NPD8455	Phase 2
0.678	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8368	Discontinued
0.677	Remote Similarity	NPD8032	Phase 2
0.6766	Remote Similarity	NPD8166	Discontinued
0.6765	Remote Similarity	NPD1512	Approved
0.675	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6651	Approved
0.674	Remote Similarity	NPD7177	Discontinued
0.6736	Remote Similarity	NPD6777	Approved
0.6736	Remote Similarity	NPD6778	Approved
0.6736	Remote Similarity	NPD6776	Approved
0.6736	Remote Similarity	NPD6780	Approved
0.6736	Remote Similarity	NPD6782	Approved
0.6736	Remote Similarity	NPD6781	Approved
0.6736	Remote Similarity	NPD6779	Approved
0.6731	Remote Similarity	NPD9717	Approved
0.6728	Remote Similarity	NPD4140	Approved
0.6724	Remote Similarity	NPD6844	Discontinued
0.6721	Remote Similarity	NPD5953	Discontinued
0.6718	Remote Similarity	NPD7696	Phase 3
0.6718	Remote Similarity	NPD7698	Approved
0.6718	Remote Similarity	NPD7697	Approved
0.6709	Remote Similarity	NPD3266	Approved
0.6709	Remote Similarity	NPD1203	Approved
0.6709	Remote Similarity	NPD3267	Approved
0.6708	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7097	Phase 1
0.6704	Remote Similarity	NPD6808	Phase 2
0.6702	Remote Similarity	NPD8361	Approved
0.6702	Remote Similarity	NPD8360	Approved
0.6687	Remote Similarity	NPD6355	Discontinued
0.6687	Remote Similarity	NPD5124	Phase 1
0.6687	Remote Similarity	NPD447	Suspended
0.6687	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1465	Phase 2
0.6685	Remote Similarity	NPD7240	Approved
0.6684	Remote Similarity	NPD7871	Phase 2
0.6684	Remote Similarity	NPD7870	Phase 2
0.6683	Remote Similarity	NPD7874	Approved
0.6683	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7783	Phase 2
0.665	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD4288	Approved
0.6646	Remote Similarity	NPD3225	Approved
0.6645	Remote Similarity	NPD17	Approved
0.6633	Remote Similarity	NPD8151	Discontinued
0.6626	Remote Similarity	NPD4307	Phase 2
0.6624	Remote Similarity	NPD3972	Approved
0.6614	Remote Similarity	NPD4287	Approved
0.6614	Remote Similarity	NPD8435	Approved
0.661	Remote Similarity	NPD7058	Phase 2
0.661	Remote Similarity	NPD7057	Phase 3
0.6609	Remote Similarity	NPD7028	Phase 2
0.6605	Remote Similarity	NPD411	Approved
0.6605	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD8320	Phase 1

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