NPASS Compound

Structure

CID289312 OpenBabel06191716092D 28 32 0 0 1 0 0 0 0 0999 V2000 2.8587 -3.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1445 -0.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0150 -0.5676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7024 -2.5160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1714 -3.0031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3962 -0.8900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8587 -3.0031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2546 -0.4198 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0150 -2.5160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7024 -1.5418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3277 -2.5160 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2336 -1.1210 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7832 -1.5027 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2806 0.0337 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8587 -1.0547 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8275 -2.1704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1714 -1.0547 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0150 -1.5418 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3277 -1.5418 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9688 -0.1018 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5460 -1.0547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6310 -1.0229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0355 0.9766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8587 -0.0805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7313 -2.5341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8430 0.3282 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 -0.3331 -2.6214 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 4 7 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 27 1 0 0 0 0 7 9 1 0 0 0 0 8 2 1 1 0 0 0 8 12 1 0 0 0 0 8 14 1 0 0 0 0 9 18 1 6 0 0 0 10 15 1 0 0 0 0 10 21 2 0 0 0 0 11 19 1 1 0 0 0 11 28 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 1 0 0 0 13 16 1 0 0 0 0 13 22 1 6 0 0 0 14 20 1 1 0 0 0 14 23 1 0 0 0 0 15 18 1 6 0 0 0 15 24 1 0 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 18 1 6 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 3 1 6 0 0 0 19 6 1 6 0 0 0 20 26 1 1 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.16
Volume:	374.106
LogP:	0.746
LogD:	0.316
LogS:	-3.791
# Rotatable Bonds:	0
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.368
Synthetic Accessibility Score:	6.632
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.441
MDCK Permeability:	5.252874325378798e-05
Pgp-inhibitor:	0.12
Pgp-substrate:	0.598
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.828

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.525
Plasma Protein Binding (PPB):	46.170188903808594%
Volume Distribution (VD):	0.436
Pgp-substrate:	51.857418060302734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.684
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.135
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	2.731
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.359
Drug-inuced Liver Injury (DILI):	0.425
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.231
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.153
Carcinogencity:	0.26
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC289312

Natural Product ID:	NPC289312
*Common Name:**	Glaucarubolone
IUPAC Name:	n.a.
Synonyms:	NSC-126764
Standard InCHIKey:	FJHVIRYYVWNHSM-RDOVZJMRSA-N
Standard InCHI:	InChI=1S/C20H26O8/c1-7-4-10(21)15(24)18(3)9(7)5-11-19-6-27-20(26,17(18)19)14(23)8(2)12(19)13(22)16(25)28-11/h4,8-9,11-15,17,22-24,26H,5-6H2,1-3H3/t8-,9+,11-,12-,13-,14-,15-,17-,18-,19+,20-/m1/s1
SMILES:	O=C1O[C@@H]2C[C@H]3C(=CC(=O)[C@H]([C@@]3([C@@H]3[C@@]42[C@@H]([C@H]1O)[C@@H](C)[C@H]([C@]3(OC4)O)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523681
PubChem CID:	10475713
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
NPO17253	Soulamea soulameoides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6619884]
NPO17253	Soulamea soulameoides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6736970]
NPO22346	Simaba cedron	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644063]
NPO17253	Soulamea soulameoides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17253	Soulamea soulameoides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22346	Simaba cedron	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6859	Eurycoma harmandiana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17253	Soulamea soulameoides	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
EC50	1
ED50	2
GI50	1
IC50	11
Others	2

Activity Type	# Activity
Cell Line	13
NON-MOLECULAR	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	400.0	nM	PMID[533670]
NPT116	Cell Line	HL-60	Homo sapiens	EC50	=	1300.0	nM	PMID[533670]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1300.0	nM	PMID[533670]
NPT116	Cell Line	HL-60	Homo sapiens	Ratio IC50	=	3.3	n.a.	PMID[533670]
NPT168	Cell Line	P388	Mus musculus	IC50	=	1.4	ug.mL-1	PMID[533671]
NPT168	Cell Line	P388	Mus musculus	T/C	=	132.0	%	PMID[533672]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.11	ug ml-1	PMID[533672]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.01	ug ml-1	PMID[533672]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	0.6	ug.mL-1	PMID[533673]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[533673]
NPT457	Cell Line	BT-549	Homo sapiens	IC50	=	0.4	ug.mL-1	PMID[533673]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[533673]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	1.5	ug.mL-1	PMID[533673]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.125	ug.mL-1	PMID[533673]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.2	ug.mL-1	PMID[533673]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	290.0	nM	PMID[533674]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	0.12	ug.mL-1	PMID[533675]

☑ 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 NPC289312 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	238
0.1-0.2	1352
0.2-0.3	4293
0.3-0.4	7817
0.4-0.5	12165
0.5-0.6	6967
0.6-0.7	5261
0.7-0.8	3840
0.8-0.85	613
0.85-0.9	90
0.9-0.95	42
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC11252
0.9903	High Similarity	NPC201992
0.981	High Similarity	NPC18547
0.981	High Similarity	NPC474906
0.9717	High Similarity	NPC152199
0.9717	High Similarity	NPC235539
0.9717	High Similarity	NPC134869
0.9714	High Similarity	NPC51978
0.9612	High Similarity	NPC293850
0.9537	High Similarity	NPC204552
0.9537	High Similarity	NPC297179
0.9537	High Similarity	NPC188667
0.9528	High Similarity	NPC49451
0.945	High Similarity	NPC476529
0.945	High Similarity	NPC475775
0.9434	High Similarity	NPC302146
0.9364	High Similarity	NPC109607
0.9364	High Similarity	NPC112038
0.9364	High Similarity	NPC107338
0.9352	High Similarity	NPC328374
0.9352	High Similarity	NPC40632
0.9352	High Similarity	NPC251236
0.9352	High Similarity	NPC96312
0.9327	High Similarity	NPC3316
0.9327	High Similarity	NPC144854
0.9279	High Similarity	NPC477046
0.9279	High Similarity	NPC102822
0.9273	High Similarity	NPC469488
0.9266	High Similarity	NPC287343
0.9266	High Similarity	NPC97908
0.9266	High Similarity	NPC474654
0.9266	High Similarity	NPC470854
0.9266	High Similarity	NPC122033
0.9266	High Similarity	NPC309433
0.9259	High Similarity	NPC473798
0.9259	High Similarity	NPC469877
0.9259	High Similarity	NPC470919
0.9252	High Similarity	NPC474516
0.9238	High Similarity	NPC277017
0.9238	High Similarity	NPC154608
0.9238	High Similarity	NPC192813
0.9182	High Similarity	NPC17772
0.9174	High Similarity	NPC474046
0.9174	High Similarity	NPC470628
0.9174	High Similarity	NPC259306
0.9167	High Similarity	NPC208998
0.9167	High Similarity	NPC7921
0.9151	High Similarity	NPC143706
0.9151	High Similarity	NPC472534
0.9091	High Similarity	NPC473968
0.9048	High Similarity	NPC102352
0.9035	High Similarity	NPC470922
0.8981	High Similarity	NPC171888
0.8981	High Similarity	NPC146945
0.8929	High Similarity	NPC470777
0.8909	High Similarity	NPC243354
0.8889	High Similarity	NPC210005
0.8868	High Similarity	NPC181357
0.8839	High Similarity	NPC251310
0.8829	High Similarity	NPC207217
0.8829	High Similarity	NPC474734
0.8818	High Similarity	NPC194100
0.8818	High Similarity	NPC194273
0.8807	High Similarity	NPC471243
0.8796	High Similarity	NPC141350
0.875	High Similarity	NPC473590
0.875	High Similarity	NPC470775
0.875	High Similarity	NPC176513
0.8739	High Similarity	NPC102088
0.8739	High Similarity	NPC268238
0.8739	High Similarity	NPC143268
0.8739	High Similarity	NPC323821
0.8739	High Similarity	NPC45218
0.8707	High Similarity	NPC24651
0.8696	High Similarity	NPC312833
0.8679	High Similarity	NPC275583
0.8673	High Similarity	NPC470776
0.8661	High Similarity	NPC16081
0.8661	High Similarity	NPC173686
0.8649	High Similarity	NPC62696
0.8649	High Similarity	NPC255017
0.8649	High Similarity	NPC293038
0.8649	High Similarity	NPC320118
0.8632	High Similarity	NPC285091
0.8624	High Similarity	NPC27814
0.8621	High Similarity	NPC67251
0.8621	High Similarity	NPC227397
0.8621	High Similarity	NPC265557
0.8621	High Similarity	NPC18945
0.8621	High Similarity	NPC105926
0.8621	High Similarity	NPC91693
0.8611	High Similarity	NPC293512
0.8611	High Similarity	NPC230541
0.8596	High Similarity	NPC127530
0.8596	High Similarity	NPC122971
0.8596	High Similarity	NPC473401
0.8596	High Similarity	NPC473920
0.8571	High Similarity	NPC472972
0.8571	High Similarity	NPC475633
0.8559	High Similarity	NPC471967
0.8559	High Similarity	NPC472002
0.8547	High Similarity	NPC476729
0.8545	High Similarity	NPC474567
0.8534	High Similarity	NPC471965
0.8532	High Similarity	NPC272576
0.8522	High Similarity	NPC471406
0.8496	Intermediate Similarity	NPC179626
0.8487	Intermediate Similarity	NPC188291
0.8475	Intermediate Similarity	NPC174367
0.8475	Intermediate Similarity	NPC47113
0.8468	Intermediate Similarity	NPC285410
0.8468	Intermediate Similarity	NPC213320
0.8468	Intermediate Similarity	NPC263827
0.8468	Intermediate Similarity	NPC250481
0.8468	Intermediate Similarity	NPC188738
0.8462	Intermediate Similarity	NPC471961
0.8462	Intermediate Similarity	NPC471964
0.8462	Intermediate Similarity	NPC262199
0.8462	Intermediate Similarity	NPC478066
0.8462	Intermediate Similarity	NPC14617
0.8462	Intermediate Similarity	NPC202666
0.8455	Intermediate Similarity	NPC310546
0.8448	Intermediate Similarity	NPC275675
0.8448	Intermediate Similarity	NPC470779
0.8448	Intermediate Similarity	NPC202051
0.8435	Intermediate Similarity	NPC319570
0.8435	Intermediate Similarity	NPC19028
0.8435	Intermediate Similarity	NPC9674
0.843	Intermediate Similarity	NPC100390
0.843	Intermediate Similarity	NPC254614
0.843	Intermediate Similarity	NPC471855
0.8426	Intermediate Similarity	NPC65523
0.8426	Intermediate Similarity	NPC475036
0.8421	Intermediate Similarity	NPC477252
0.8421	Intermediate Similarity	NPC470171
0.8407	Intermediate Similarity	NPC472274
0.8403	Intermediate Similarity	NPC470780
0.8393	Intermediate Similarity	NPC205534
0.8393	Intermediate Similarity	NPC474927
0.8393	Intermediate Similarity	NPC473397
0.8393	Intermediate Similarity	NPC477253
0.8393	Intermediate Similarity	NPC280782
0.8393	Intermediate Similarity	NPC116794
0.8393	Intermediate Similarity	NPC90769
0.8393	Intermediate Similarity	NPC130427
0.839	Intermediate Similarity	NPC247315
0.839	Intermediate Similarity	NPC473255
0.839	Intermediate Similarity	NPC30188
0.839	Intermediate Similarity	NPC471962
0.839	Intermediate Similarity	NPC470477
0.839	Intermediate Similarity	NPC177820
0.839	Intermediate Similarity	NPC471963
0.8378	Intermediate Similarity	NPC108709
0.8378	Intermediate Similarity	NPC75747
0.8378	Intermediate Similarity	NPC274507
0.8378	Intermediate Similarity	NPC137104
0.8378	Intermediate Similarity	NPC471093
0.8378	Intermediate Similarity	NPC68419
0.8378	Intermediate Similarity	NPC474786
0.8378	Intermediate Similarity	NPC199457
0.8378	Intermediate Similarity	NPC85391
0.8378	Intermediate Similarity	NPC7870
0.8378	Intermediate Similarity	NPC102914
0.8378	Intermediate Similarity	NPC220984
0.8378	Intermediate Similarity	NPC110139
0.8378	Intermediate Similarity	NPC320383
0.8376	Intermediate Similarity	NPC222688
0.8376	Intermediate Similarity	NPC40775
0.8376	Intermediate Similarity	NPC107966
0.8376	Intermediate Similarity	NPC249848
0.8376	Intermediate Similarity	NPC235438
0.8364	Intermediate Similarity	NPC473410
0.8364	Intermediate Similarity	NPC473288
0.8364	Intermediate Similarity	NPC94942
0.8364	Intermediate Similarity	NPC471094
0.8364	Intermediate Similarity	NPC258323
0.8364	Intermediate Similarity	NPC63841
0.8364	Intermediate Similarity	NPC469984
0.8348	Intermediate Similarity	NPC286347
0.8347	Intermediate Similarity	NPC45346
0.8347	Intermediate Similarity	NPC475377
0.8347	Intermediate Similarity	NPC478065
0.8347	Intermediate Similarity	NPC172374
0.8347	Intermediate Similarity	NPC173435
0.8347	Intermediate Similarity	NPC264566
0.8347	Intermediate Similarity	NPC476074
0.8347	Intermediate Similarity	NPC478064
0.8347	Intermediate Similarity	NPC301639
0.8347	Intermediate Similarity	NPC134914
0.8347	Intermediate Similarity	NPC475167
0.8347	Intermediate Similarity	NPC329993
0.8347	Intermediate Similarity	NPC262796
0.8333	Intermediate Similarity	NPC295220
0.8333	Intermediate Similarity	NPC475636
0.8333	Intermediate Similarity	NPC474575
0.8319	Intermediate Similarity	NPC225049
0.8319	Intermediate Similarity	NPC178981
0.8319	Intermediate Similarity	NPC271138
0.8319	Intermediate Similarity	NPC260665
0.8319	Intermediate Similarity	NPC87662

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 NPC289312 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1609
0.2-0.3	3793
0.3-0.4	2247
0.4-0.5	730
0.5-0.6	278
0.6-0.7	134
0.7-0.8	133
0.8-0.85	20
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	NPD8328	Phase 3
0.8205	Intermediate Similarity	NPD6319	Approved
0.8158	Intermediate Similarity	NPD4632	Approved
0.8125	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD6412	Phase 2
0.8103	Intermediate Similarity	NPD6009	Approved
0.8103	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8083	Intermediate Similarity	NPD7492	Approved
0.807	Intermediate Similarity	NPD8297	Approved
0.807	Intermediate Similarity	NPD6882	Approved
0.8051	Intermediate Similarity	NPD6059	Approved
0.8051	Intermediate Similarity	NPD6054	Approved
0.8033	Intermediate Similarity	NPD7736	Approved
0.8018	Intermediate Similarity	NPD7128	Approved
0.8018	Intermediate Similarity	NPD5739	Approved
0.8018	Intermediate Similarity	NPD6675	Approved
0.8018	Intermediate Similarity	NPD6402	Approved
0.8017	Intermediate Similarity	NPD6616	Approved
0.7983	Intermediate Similarity	NPD6015	Approved
0.7983	Intermediate Similarity	NPD6016	Approved
0.7965	Intermediate Similarity	NPD6373	Approved
0.7965	Intermediate Similarity	NPD6372	Approved
0.7951	Intermediate Similarity	NPD7078	Approved
0.7951	Intermediate Similarity	NPD8293	Discontinued
0.7946	Intermediate Similarity	NPD5701	Approved
0.7946	Intermediate Similarity	NPD5697	Approved
0.7917	Intermediate Similarity	NPD6370	Approved
0.7917	Intermediate Similarity	NPD5988	Approved
0.7876	Intermediate Similarity	NPD6881	Approved
0.7876	Intermediate Similarity	NPD6899	Approved
0.7876	Intermediate Similarity	NPD6686	Approved
0.7876	Intermediate Similarity	NPD7320	Approved
0.7869	Intermediate Similarity	NPD7507	Approved
0.7826	Intermediate Similarity	NPD6649	Approved
0.7826	Intermediate Similarity	NPD6650	Approved
0.7807	Intermediate Similarity	NPD6013	Approved
0.7807	Intermediate Similarity	NPD6014	Approved
0.7807	Intermediate Similarity	NPD6012	Approved
0.7739	Intermediate Similarity	NPD7102	Approved
0.7739	Intermediate Similarity	NPD6883	Approved
0.7739	Intermediate Similarity	NPD7290	Approved
0.7719	Intermediate Similarity	NPD6011	Approved
0.7719	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD4755	Approved
0.7699	Intermediate Similarity	NPD6008	Approved
0.7686	Intermediate Similarity	NPD5983	Phase 2
0.768	Intermediate Similarity	NPD7319	Approved
0.7672	Intermediate Similarity	NPD6617	Approved
0.7672	Intermediate Similarity	NPD6869	Approved
0.7672	Intermediate Similarity	NPD6847	Approved
0.7672	Intermediate Similarity	NPD8130	Phase 1
0.7652	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7748	Approved
0.7586	Intermediate Similarity	NPD4634	Approved
0.757	Intermediate Similarity	NPD7515	Phase 2
0.7568	Intermediate Similarity	NPD5285	Approved
0.7568	Intermediate Similarity	NPD5286	Approved
0.7568	Intermediate Similarity	NPD4700	Approved
0.7568	Intermediate Similarity	NPD4696	Approved
0.7561	Intermediate Similarity	NPD7604	Phase 2
0.7545	Intermediate Similarity	NPD7902	Approved
0.7521	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6033	Approved
0.7455	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5222	Approved
0.7455	Intermediate Similarity	NPD5221	Approved
0.7455	Intermediate Similarity	NPD4697	Phase 3
0.744	Intermediate Similarity	NPD6336	Discontinued
0.7436	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD5224	Approved
0.7434	Intermediate Similarity	NPD5226	Approved
0.7434	Intermediate Similarity	NPD5211	Phase 2
0.7434	Intermediate Similarity	NPD4633	Approved
0.7434	Intermediate Similarity	NPD5225	Approved
0.7417	Intermediate Similarity	NPD6274	Approved
0.7391	Intermediate Similarity	NPD4767	Approved
0.7391	Intermediate Similarity	NPD4768	Approved
0.7387	Intermediate Similarity	NPD5173	Approved
0.7387	Intermediate Similarity	NPD6084	Phase 2
0.7387	Intermediate Similarity	NPD6083	Phase 2
0.7383	Intermediate Similarity	NPD5328	Approved
0.7377	Intermediate Similarity	NPD7516	Approved
0.7368	Intermediate Similarity	NPD5175	Approved
0.7368	Intermediate Similarity	NPD5174	Approved
0.7358	Intermediate Similarity	NPD3573	Approved
0.7355	Intermediate Similarity	NPD7115	Discovery
0.7345	Intermediate Similarity	NPD5223	Approved
0.7339	Intermediate Similarity	NPD6399	Phase 3
0.7321	Intermediate Similarity	NPD7638	Approved
0.7321	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD5141	Approved
0.7295	Intermediate Similarity	NPD7328	Approved
0.7295	Intermediate Similarity	NPD7327	Approved
0.7273	Intermediate Similarity	NPD7900	Approved
0.7273	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD4729	Approved
0.7265	Intermediate Similarity	NPD4730	Approved
0.7264	Intermediate Similarity	NPD3618	Phase 1
0.7258	Intermediate Similarity	NPD8517	Approved
0.7258	Intermediate Similarity	NPD8516	Approved
0.7258	Intermediate Similarity	NPD8513	Phase 3
0.7258	Intermediate Similarity	NPD8515	Approved
0.7258	Intermediate Similarity	NPD8033	Approved
0.7257	Intermediate Similarity	NPD7639	Approved
0.7257	Intermediate Similarity	NPD7640	Approved
0.725	Intermediate Similarity	NPD8133	Approved
0.7248	Intermediate Similarity	NPD6079	Approved
0.7236	Intermediate Similarity	NPD7101	Approved
0.7236	Intermediate Similarity	NPD7100	Approved
0.7217	Intermediate Similarity	NPD4754	Approved
0.7213	Intermediate Similarity	NPD6317	Approved
0.7207	Intermediate Similarity	NPD5695	Phase 3
0.7179	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD8377	Approved
0.7177	Intermediate Similarity	NPD8294	Approved
0.7168	Intermediate Similarity	NPD5696	Approved
0.7154	Intermediate Similarity	NPD6313	Approved
0.7154	Intermediate Similarity	NPD6314	Approved
0.7154	Intermediate Similarity	NPD6335	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD6067	Discontinued
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5250	Approved
0.7131	Intermediate Similarity	NPD6868	Approved
0.713	Intermediate Similarity	NPD6672	Approved
0.713	Intermediate Similarity	NPD5737	Approved
0.712	Intermediate Similarity	NPD7503	Approved
0.712	Intermediate Similarity	NPD8380	Approved
0.712	Intermediate Similarity	NPD8379	Approved
0.712	Intermediate Similarity	NPD6908	Approved
0.712	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6909	Approved
0.712	Intermediate Similarity	NPD6921	Approved
0.712	Intermediate Similarity	NPD8335	Approved
0.712	Intermediate Similarity	NPD8378	Approved
0.712	Intermediate Similarity	NPD8296	Approved
0.7119	Intermediate Similarity	NPD5128	Approved
0.7091	Intermediate Similarity	NPD6411	Approved
0.7083	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD4753	Phase 2
0.7048	Intermediate Similarity	NPD3667	Approved
0.7027	Intermediate Similarity	NPD4202	Approved
0.7	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD46	Approved
0.6972	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5282	Discontinued
0.6944	Remote Similarity	NPD7334	Approved
0.6944	Remote Similarity	NPD6684	Approved
0.6944	Remote Similarity	NPD6409	Approved
0.6944	Remote Similarity	NPD7521	Approved
0.6944	Remote Similarity	NPD5330	Approved
0.6944	Remote Similarity	NPD7146	Approved
0.6942	Remote Similarity	NPD5216	Approved
0.6942	Remote Similarity	NPD5215	Approved
0.6942	Remote Similarity	NPD5217	Approved
0.6916	Remote Similarity	NPD3665	Phase 1
0.6916	Remote Similarity	NPD3133	Approved
0.6916	Remote Similarity	NPD3666	Approved
0.6916	Remote Similarity	NPD4786	Approved
0.6909	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6101	Approved
0.6894	Remote Similarity	NPD7260	Phase 2
0.6864	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5135	Approved
0.686	Remote Similarity	NPD5169	Approved
0.686	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4695	Discontinued
0.6846	Remote Similarity	NPD8074	Phase 3
0.6833	Remote Similarity	NPD5168	Approved
0.6818	Remote Similarity	NPD5956	Approved
0.6818	Remote Similarity	NPD6903	Approved
0.6803	Remote Similarity	NPD5127	Approved
0.6789	Remote Similarity	NPD5279	Phase 3
0.6786	Remote Similarity	NPD8034	Phase 2
0.6786	Remote Similarity	NPD8035	Phase 2
0.6757	Remote Similarity	NPD6904	Approved
0.6757	Remote Similarity	NPD6673	Approved
0.6757	Remote Similarity	NPD6080	Approved
0.6754	Remote Similarity	NPD5210	Approved
0.6754	Remote Similarity	NPD4629	Approved
0.6754	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6053	Discontinued
0.6726	Remote Similarity	NPD5779	Approved
0.6726	Remote Similarity	NPD5778	Approved
0.6716	Remote Similarity	NPD6845	Suspended
0.6697	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7632	Discontinued
0.664	Remote Similarity	NPD5167	Approved
0.6637	Remote Similarity	NPD5693	Phase 1
0.6637	Remote Similarity	NPD7983	Approved
0.6612	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5344	Discontinued
0.6609	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD3668	Phase 3
0.6606	Remote Similarity	NPD4197	Approved
0.6594	Remote Similarity	NPD6334	Approved
0.6594	Remote Similarity	NPD6333	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