NPASS Compound

Structure

NPC470775 OpenBabel07101718332D 30 34 0 0 1 0 0 0 0 0999 V2000 0.6637 1.2495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9107 -2.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2901 0.9676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2418 1.2945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4576 -1.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7666 -1.8328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2801 -0.8622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8972 -1.8159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3270 -1.4980 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4478 -0.8284 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1965 -1.5149 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8347 0.1195 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7471 -0.5274 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8776 -0.5104 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3836 0.5914 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0973 -0.2673 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2815 -0.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3172 -0.8453 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1867 -0.8622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7334 0.5329 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4668 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2260 -0.3634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6969 0.3997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8505 1.3025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7021 1.4401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4593 0.9295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1739 -1.0863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9566 0.7629 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 -1.8805 -1.4822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 8 1 0 0 0 0 4 20 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 11 1 0 0 0 0 7 19 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 9 18 1 1 0 0 0 10 14 1 0 0 0 0 10 22 1 6 0 0 0 11 19 1 1 0 0 0 11 30 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 1 0 0 0 13 18 1 1 0 0 0 13 19 1 0 0 0 0 14 18 1 1 0 0 0 14 24 1 0 0 0 0 15 20 1 6 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 6 0 0 0 16 26 1 0 0 0 0 17 27 2 0 0 0 0 17 30 1 0 0 0 0 18 3 1 1 0 0 0 19 21 1 6 0 0 0 20 21 1 1 0 0 0 20 29 1 0 0 0 0 21 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.19
Volume:	402.829
LogP:	0.597
LogD:	-0.099
LogS:	-3.07
# Rotatable Bonds:	1
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.211
Synthetic Accessibility Score:	6.868
Fsp3:	0.857
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:	-6.045
MDCK Permeability:	6.74282928230241e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.103
20% Bioavailability (F20%):	0.062
30% Bioavailability (F30%):	0.864

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	30.36115264892578%
Volume Distribution (VD):	0.339
Pgp-substrate:	46.41706466674805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.381
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.525
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.062

ADMET: Excretion

Clearance (CL):	1.951
Half-life (T1/2):	0.675

ADMET: Toxicity

hERG Blockers:	0.099
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.104
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.489
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.172
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.929

Download Data

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

Natural Product: NPC470775

Natural Product ID:	NPC470775
*Common Name:**	Bruceine F
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BGIPVDXBBKWRAU-PCALDACFSA-N
Standard InCHI:	InChI=1S/C21H30O9/c1-4-20-15(25)12(23)13-18(3)9(8(2)5-10(22)14(18)24)6-11-19(13,7-29-20)21(20,28)16(26)17(27)30-11/h5,9-16,22-26,28H,4,6-7H2,1-3H3/t9-,10-,11+,12+,13+,14+,15-,16-,18-,19+,20-,21-/m0/s1
SMILES:	CCC12C(C(C3C4(C(CC5C3(C1(C(C(=O)O5)O)O)CO2)C(=CC(C4O)O)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2227687
PubChem CID:	76315043
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/0031-9422(96)00258-0]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S1383-5769(99)00023-9]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10086989]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1512598]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15165151]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	fruit	Indonesia	n.a.	PMID[17896817]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	Vietnam	n.a.	PMID[19026551]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20050684]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22506620]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6481366]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561896]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14948	Brucea javanica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14948	Brucea javanica	Species	Simaroubaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	31.2	%	PMID[450172]

☑ 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 NPC470775 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	244
0.1-0.2	1444
0.2-0.3	4039
0.3-0.4	7348
0.4-0.5	12130
0.5-0.6	7836
0.6-0.7	5509
0.7-0.8	3610
0.8-0.85	398
0.85-0.9	83
0.9-0.95	52
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC176513
0.9725	High Similarity	NPC470776
0.9545	High Similarity	NPC251310
0.9541	High Similarity	NPC474734
0.9455	High Similarity	NPC470854
0.9455	High Similarity	NPC122033
0.9455	High Similarity	NPC287343
0.9455	High Similarity	NPC474654
0.9455	High Similarity	NPC97908
0.9375	High Similarity	NPC112038
0.9298	High Similarity	NPC67251
0.9279	High Similarity	NPC473590
0.9266	High Similarity	NPC302146
0.9196	High Similarity	NPC17772
0.9196	High Similarity	NPC204552
0.9196	High Similarity	NPC188667
0.9189	High Similarity	NPC259306
0.9189	High Similarity	NPC474046
0.9189	High Similarity	NPC179626
0.9189	High Similarity	NPC470628
0.9182	High Similarity	NPC7921
0.9182	High Similarity	NPC49451
0.9182	High Similarity	NPC208998
0.9123	High Similarity	NPC477046
0.9123	High Similarity	NPC102822
0.9099	High Similarity	NPC469877
0.9099	High Similarity	NPC470919
0.9099	High Similarity	NPC117712
0.906	High Similarity	NPC470780
0.9052	High Similarity	NPC24651
0.9052	High Similarity	NPC476729
0.9043	High Similarity	NPC312833
0.9018	High Similarity	NPC40632
0.9018	High Similarity	NPC328374
0.9018	High Similarity	NPC251236
0.9018	High Similarity	NPC96312
0.9	High Similarity	NPC146945
0.9	High Similarity	NPC171888
0.8991	High Similarity	NPC141350
0.8991	High Similarity	NPC472534
0.8991	High Similarity	NPC143706
0.8966	High Similarity	NPC105926
0.8966	High Similarity	NPC18945
0.8966	High Similarity	NPC91693
0.8966	High Similarity	NPC265557
0.8947	High Similarity	NPC470777
0.8947	High Similarity	NPC469488
0.8929	High Similarity	NPC473798
0.8919	High Similarity	NPC472002
0.8889	High Similarity	NPC470922
0.886	High Similarity	NPC297179
0.885	High Similarity	NPC207217
0.8839	High Similarity	NPC51978
0.8807	High Similarity	NPC230541
0.8793	High Similarity	NPC470779
0.8761	High Similarity	NPC268238
0.8761	High Similarity	NPC143268
0.8761	High Similarity	NPC323821
0.8761	High Similarity	NPC45218
0.875	High Similarity	NPC474516
0.875	High Similarity	NPC11252
0.875	High Similarity	NPC289312
0.8739	High Similarity	NPC476008
0.8727	High Similarity	NPC293850
0.8718	High Similarity	NPC222688
0.8684	High Similarity	NPC16081
0.8684	High Similarity	NPC235539
0.8684	High Similarity	NPC134869
0.8684	High Similarity	NPC152199
0.8684	High Similarity	NPC173686
0.8661	High Similarity	NPC201992
0.8661	High Similarity	NPC157476
0.8655	High Similarity	NPC181999
0.8655	High Similarity	NPC225049
0.8655	High Similarity	NPC477745
0.8636	High Similarity	NPC144854
0.8636	High Similarity	NPC3316
0.8624	High Similarity	NPC258532
0.8624	High Similarity	NPC475036
0.8621	High Similarity	NPC475775
0.8621	High Similarity	NPC476529
0.8609	High Similarity	NPC469684
0.8609	High Similarity	NPC473968
0.8609	High Similarity	NPC470171
0.8609	High Similarity	NPC477116
0.8609	High Similarity	NPC27999
0.8596	High Similarity	NPC474906
0.8596	High Similarity	NPC18547
0.8584	High Similarity	NPC269530
0.8583	High Similarity	NPC470882
0.8559	High Similarity	NPC192813
0.8559	High Similarity	NPC154608
0.8559	High Similarity	NPC277017
0.8547	High Similarity	NPC109607
0.8547	High Similarity	NPC107338
0.8522	High Similarity	NPC89929
0.8512	High Similarity	NPC188291
0.8509	High Similarity	NPC94509
0.8509	High Similarity	NPC477266
0.8482	Intermediate Similarity	NPC42662
0.8468	Intermediate Similarity	NPC242486
0.8468	Intermediate Similarity	NPC15215
0.8462	Intermediate Similarity	NPC268958
0.8462	Intermediate Similarity	NPC122971
0.8455	Intermediate Similarity	NPC102316
0.8448	Intermediate Similarity	NPC98249
0.8448	Intermediate Similarity	NPC146432
0.8448	Intermediate Similarity	NPC470778
0.8448	Intermediate Similarity	NPC53396
0.8448	Intermediate Similarity	NPC58662
0.8435	Intermediate Similarity	NPC243354
0.8435	Intermediate Similarity	NPC299849
0.843	Intermediate Similarity	NPC473265
0.8407	Intermediate Similarity	NPC5103
0.8403	Intermediate Similarity	NPC269642
0.8393	Intermediate Similarity	NPC208461
0.8393	Intermediate Similarity	NPC289702
0.839	Intermediate Similarity	NPC472004
0.8387	Intermediate Similarity	NPC168879
0.8378	Intermediate Similarity	NPC102352
0.8376	Intermediate Similarity	NPC284707
0.8362	Intermediate Similarity	NPC213084
0.8362	Intermediate Similarity	NPC190185
0.8348	Intermediate Similarity	NPC194273
0.8348	Intermediate Similarity	NPC477126
0.8347	Intermediate Similarity	NPC293112
0.8333	Intermediate Similarity	NPC469656
0.8333	Intermediate Similarity	NPC478066
0.8333	Intermediate Similarity	NPC243014
0.8333	Intermediate Similarity	NPC188738
0.8333	Intermediate Similarity	NPC251998
0.8333	Intermediate Similarity	NPC471243
0.8333	Intermediate Similarity	NPC469655
0.8333	Intermediate Similarity	NPC474846
0.8333	Intermediate Similarity	NPC472003
0.8319	Intermediate Similarity	NPC472401
0.8319	Intermediate Similarity	NPC75417
0.8305	Intermediate Similarity	NPC473636
0.8305	Intermediate Similarity	NPC77689
0.8304	Intermediate Similarity	NPC59530
0.8293	Intermediate Similarity	NPC231529
0.8293	Intermediate Similarity	NPC470880
0.8291	Intermediate Similarity	NPC134430
0.8291	Intermediate Similarity	NPC476713
0.8291	Intermediate Similarity	NPC476712
0.8291	Intermediate Similarity	NPC296822
0.8279	Intermediate Similarity	NPC473253
0.8276	Intermediate Similarity	NPC472274
0.8276	Intermediate Similarity	NPC247069
0.8268	Intermediate Similarity	NPC295885
0.8268	Intermediate Similarity	NPC596
0.8268	Intermediate Similarity	NPC140045
0.8264	Intermediate Similarity	NPC470477
0.8264	Intermediate Similarity	NPC172154
0.8264	Intermediate Similarity	NPC81736
0.8264	Intermediate Similarity	NPC473255
0.8261	Intermediate Similarity	NPC174836
0.8261	Intermediate Similarity	NPC473877
0.8261	Intermediate Similarity	NPC280782
0.8257	Intermediate Similarity	NPC477656
0.8257	Intermediate Similarity	NPC477655
0.8254	Intermediate Similarity	NPC262813
0.825	Intermediate Similarity	NPC235438
0.825	Intermediate Similarity	NPC249848
0.825	Intermediate Similarity	NPC19464
0.825	Intermediate Similarity	NPC107966
0.825	Intermediate Similarity	NPC40775
0.8246	Intermediate Similarity	NPC210005
0.824	Intermediate Similarity	NPC478151
0.8235	Intermediate Similarity	NPC475003
0.8235	Intermediate Similarity	NPC109973
0.8235	Intermediate Similarity	NPC478051
0.823	Intermediate Similarity	NPC472218
0.823	Intermediate Similarity	NPC37628
0.823	Intermediate Similarity	NPC472219
0.823	Intermediate Similarity	NPC472217
0.8226	Intermediate Similarity	NPC301639
0.8226	Intermediate Similarity	NPC264566
0.8226	Intermediate Similarity	NPC475167
0.8226	Intermediate Similarity	NPC173435
0.8226	Intermediate Similarity	NPC262796
0.8226	Intermediate Similarity	NPC45346
0.8226	Intermediate Similarity	NPC172374
0.8226	Intermediate Similarity	NPC478064
0.8226	Intermediate Similarity	NPC476074
0.8226	Intermediate Similarity	NPC329993
0.8226	Intermediate Similarity	NPC475377
0.8226	Intermediate Similarity	NPC134914
0.8226	Intermediate Similarity	NPC478065
0.822	Intermediate Similarity	NPC108581
0.822	Intermediate Similarity	NPC478206
0.822	Intermediate Similarity	NPC240509
0.822	Intermediate Similarity	NPC478205
0.822	Intermediate Similarity	NPC21326
0.822	Intermediate Similarity	NPC286347
0.8214	Intermediate Similarity	NPC477877
0.8214	Intermediate Similarity	NPC181357
0.8205	Intermediate Similarity	NPC476710
0.8205	Intermediate Similarity	NPC49492
0.8205	Intermediate Similarity	NPC266728

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 NPC470775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	1645
0.2-0.3	3712
0.3-0.4	2267
0.4-0.5	735
0.5-0.6	318
0.6-0.7	170
0.7-0.8	92
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
0.8393	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7983	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD6319	Approved
0.7886	Intermediate Similarity	NPD8328	Phase 3
0.7845	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD8516	Approved
0.7724	Intermediate Similarity	NPD8513	Phase 3
0.7724	Intermediate Similarity	NPD8515	Approved
0.7724	Intermediate Similarity	NPD8517	Approved
0.7724	Intermediate Similarity	NPD6921	Approved
0.7717	Intermediate Similarity	NPD7319	Approved
0.7686	Intermediate Similarity	NPD7115	Discovery
0.7679	Intermediate Similarity	NPD4225	Approved
0.7583	Intermediate Similarity	NPD4632	Approved
0.7542	Intermediate Similarity	NPD6372	Approved
0.7542	Intermediate Similarity	NPD6373	Approved
0.7542	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD7492	Approved
0.7521	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6054	Approved
0.75	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD7736	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.748	Intermediate Similarity	NPD7507	Approved
0.748	Intermediate Similarity	NPD6616	Approved
0.744	Intermediate Similarity	NPD6015	Approved
0.744	Intermediate Similarity	NPD6016	Approved
0.7436	Intermediate Similarity	NPD6402	Approved
0.7436	Intermediate Similarity	NPD5739	Approved
0.7436	Intermediate Similarity	NPD7128	Approved
0.7436	Intermediate Similarity	NPD6675	Approved
0.7422	Intermediate Similarity	NPD7078	Approved
0.7422	Intermediate Similarity	NPD8293	Discontinued
0.7417	Intermediate Similarity	NPD6650	Approved
0.7417	Intermediate Similarity	NPD6649	Approved
0.7381	Intermediate Similarity	NPD5988	Approved
0.7381	Intermediate Similarity	NPD6370	Approved
0.7373	Intermediate Similarity	NPD5701	Approved
0.7373	Intermediate Similarity	NPD5697	Approved
0.7333	Intermediate Similarity	NPD4634	Approved
0.7311	Intermediate Similarity	NPD6686	Approved
0.7311	Intermediate Similarity	NPD7320	Approved
0.7311	Intermediate Similarity	NPD6899	Approved
0.7311	Intermediate Similarity	NPD6881	Approved
0.7288	Intermediate Similarity	NPD6008	Approved
0.7287	Intermediate Similarity	NPD8074	Phase 3
0.728	Intermediate Similarity	NPD7516	Approved
0.7273	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6009	Approved
0.725	Intermediate Similarity	NPD6014	Approved
0.725	Intermediate Similarity	NPD6013	Approved
0.725	Intermediate Similarity	NPD6012	Approved
0.7232	Intermediate Similarity	NPD5778	Approved
0.7232	Intermediate Similarity	NPD5779	Approved
0.7213	Intermediate Similarity	NPD6882	Approved
0.72	Intermediate Similarity	NPD7327	Approved
0.72	Intermediate Similarity	NPD7328	Approved
0.719	Intermediate Similarity	NPD6883	Approved
0.719	Intermediate Similarity	NPD7102	Approved
0.719	Intermediate Similarity	NPD7290	Approved
0.7179	Intermediate Similarity	NPD5211	Phase 2
0.7167	Intermediate Similarity	NPD6011	Approved
0.7165	Intermediate Similarity	NPD5983	Phase 2
0.7155	Intermediate Similarity	NPD7640	Approved
0.7155	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD7983	Approved
0.7131	Intermediate Similarity	NPD6869	Approved
0.7131	Intermediate Similarity	NPD6847	Approved
0.7131	Intermediate Similarity	NPD8130	Phase 1
0.7131	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD4755	Approved
0.7083	Intermediate Similarity	NPD6412	Phase 2
0.708	Intermediate Similarity	NPD6399	Phase 3
0.7069	Intermediate Similarity	NPD7638	Approved
0.7059	Intermediate Similarity	NPD5141	Approved
0.7054	Intermediate Similarity	NPD7604	Phase 2
0.7016	Intermediate Similarity	NPD8133	Approved
0.7009	Intermediate Similarity	NPD5286	Approved
0.7009	Intermediate Similarity	NPD4700	Approved
0.7009	Intermediate Similarity	NPD4696	Approved
0.7009	Intermediate Similarity	NPD5285	Approved
0.6992	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7902	Approved
0.697	Remote Similarity	NPD6033	Approved
0.6964	Remote Similarity	NPD6101	Approved
0.6964	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5344	Discontinued
0.6947	Remote Similarity	NPD6336	Discontinued
0.6942	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6274	Approved
0.6899	Remote Similarity	NPD8379	Approved
0.6899	Remote Similarity	NPD8033	Approved
0.6899	Remote Similarity	NPD8335	Approved
0.6899	Remote Similarity	NPD8296	Approved
0.6899	Remote Similarity	NPD8380	Approved
0.6899	Remote Similarity	NPD8378	Approved
0.6897	Remote Similarity	NPD4697	Phase 3
0.6891	Remote Similarity	NPD4633	Approved
0.6891	Remote Similarity	NPD5226	Approved
0.6891	Remote Similarity	NPD5225	Approved
0.6891	Remote Similarity	NPD5224	Approved
0.687	Remote Similarity	NPD7748	Approved
0.687	Remote Similarity	NPD5282	Discontinued
0.686	Remote Similarity	NPD4768	Approved
0.686	Remote Similarity	NPD4767	Approved
0.6842	Remote Similarity	NPD7515	Phase 2
0.6842	Remote Similarity	NPD7637	Suspended
0.6838	Remote Similarity	NPD6084	Phase 2
0.6838	Remote Similarity	NPD6083	Phase 2
0.6833	Remote Similarity	NPD5174	Approved
0.6833	Remote Similarity	NPD5175	Approved
0.6822	Remote Similarity	NPD8294	Approved
0.6822	Remote Similarity	NPD8377	Approved
0.6807	Remote Similarity	NPD1700	Approved
0.6807	Remote Similarity	NPD5223	Approved
0.6786	Remote Similarity	NPD3573	Approved
0.678	Remote Similarity	NPD5696	Approved
0.6774	Remote Similarity	NPD6371	Approved
0.6769	Remote Similarity	NPD7503	Approved
0.6769	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD46	Approved
0.6754	Remote Similarity	NPD6698	Approved
0.6752	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5222	Approved
0.6752	Remote Similarity	NPD5221	Approved
0.6748	Remote Similarity	NPD4729	Approved
0.6748	Remote Similarity	NPD4730	Approved
0.6744	Remote Similarity	NPD7101	Approved
0.6744	Remote Similarity	NPD7100	Approved
0.6724	Remote Similarity	NPD7900	Approved
0.6724	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6317	Approved
0.6696	Remote Similarity	NPD8035	Phase 2
0.6696	Remote Similarity	NPD8034	Phase 2
0.6696	Remote Similarity	NPD3618	Phase 1
0.6695	Remote Similarity	NPD5173	Approved
0.6694	Remote Similarity	NPD4754	Approved
0.6691	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6313	Approved
0.6641	Remote Similarity	NPD6909	Approved
0.6641	Remote Similarity	NPD6908	Approved
0.664	Remote Similarity	NPD5248	Approved
0.664	Remote Similarity	NPD5251	Approved
0.664	Remote Similarity	NPD5250	Approved
0.664	Remote Similarity	NPD5247	Approved
0.664	Remote Similarity	NPD5249	Phase 3
0.6637	Remote Similarity	NPD7524	Approved
0.6636	Remote Similarity	NPD3667	Approved
0.6613	Remote Similarity	NPD5128	Approved
0.6612	Remote Similarity	NPD7632	Discontinued
0.6583	Remote Similarity	NPD6648	Approved
0.6552	Remote Similarity	NPD6079	Approved
0.6525	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6845	Suspended
0.6522	Remote Similarity	NPD4753	Phase 2
0.6518	Remote Similarity	NPD4786	Approved
0.6512	Remote Similarity	NPD6868	Approved
0.6496	Remote Similarity	NPD4202	Approved
0.6471	Remote Similarity	NPD7839	Suspended
0.646	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5216	Approved
0.6457	Remote Similarity	NPD5217	Approved
0.6457	Remote Similarity	NPD5215	Approved
0.6435	Remote Similarity	NPD6672	Approved
0.6435	Remote Similarity	NPD5737	Approved
0.6404	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4629	Approved
0.6387	Remote Similarity	NPD5210	Approved
0.6387	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5169	Approved
0.6378	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5135	Approved
0.6377	Remote Similarity	NPD5956	Approved
0.6372	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5127	Approved
0.6316	Remote Similarity	NPD1694	Approved
0.6296	Remote Similarity	NPD6067	Discontinued
0.6294	Remote Similarity	NPD6333	Approved
0.6294	Remote Similarity	NPD6334	Approved
0.6293	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6695	Phase 3
0.6271	Remote Similarity	NPD5693	Phase 1
0.6261	Remote Similarity	NPD7146	Approved
0.6261	Remote Similarity	NPD7334	Approved
0.6261	Remote Similarity	NPD6684	Approved
0.6261	Remote Similarity	NPD6409	Approved
0.6261	Remote Similarity	NPD5786	Approved
0.6261	Remote Similarity	NPD5330	Approved
0.6261	Remote Similarity	NPD7521	Approved
0.6261	Remote Similarity	NPD6098	Approved
0.625	Remote Similarity	NPD8299	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