NPASS Compound

Structure

NPC102822 OpenBabel07101718292D 30 35 0 0 1 0 0 0 0 0999 V2000 -4.7631 -0.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 -1.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8971 -1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4330 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8971 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 -0.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0311 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 1.2500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1651 -1.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6045 2.0015 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2990 2.3360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 -0.2500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4330 -0.2500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1651 -0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2990 0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4330 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4330 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4330 1.2500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0311 -3.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 -2.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1773 2.6250 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 3.3360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6732 -1.7207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1351 2.0730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9330 1.6160 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 -1.9935 2.0015 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 3 7 2 0 0 0 0 3 9 1 0 0 0 0 4 8 1 0 0 0 0 4 10 1 0 0 0 0 5 17 1 0 0 0 0 5 29 1 0 0 0 0 6 18 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 8 16 1 6 0 0 0 9 11 1 0 0 0 0 9 21 2 0 0 0 0 10 17 1 1 0 0 0 10 30 1 0 0 0 0 11 16 1 6 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 6 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 13 30 1 0 0 0 0 14 16 1 6 0 0 0 14 17 1 0 0 0 0 14 19 1 0 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 15 25 1 0 0 0 0 16 2 1 6 0 0 0 17 20 1 1 0 0 0 18 20 1 6 0 0 0 18 28 1 0 0 0 0 19 26 1 1 0 0 0 19 29 1 0 0 0 0 20 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.14
Volume:	383.13
LogP:	0.517
LogD:	-0.216
LogS:	-3.929
# Rotatable Bonds:	0
TPSA:	163.12
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	7.17
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.634
MDCK Permeability:	4.248539335094392e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.926

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.313
Plasma Protein Binding (PPB):	31.607158660888672%
Volume Distribution (VD):	0.356
Pgp-substrate:	69.00301361083984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.485
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	1.842
Half-life (T1/2):	0.174

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.562
AMES Toxicity:	0.663
Rat Oral Acute Toxicity:	0.379
Maximum Recommended Daily Dose:	0.491
Skin Sensitization:	0.376
Carcinogencity:	0.545
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC102822

Natural Product ID:	NPC102822
*Common Name:**	MOCOVNGOINOTNW-XXJDAYKBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MOCOVNGOINOTNW-XXJDAYKBSA-N
Standard InCHI:	InChI=1S/C20H24O10/c1-7-3-9(21)11(22)16(2)8(7)4-10-17-5-29-19(26,14(16)17)15(25)18(6-28-18)20(17,27)12(23)13(24)30-10/h3,8,10-12,14-15,22-23,25-27H,4-6H2,1-2H3/t8-,10+,11+,12-,14+,15+,16+,17+,18-,19-,20-/m0/s1
SMILES:	CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@H]1OC(=O)[C@@H]([C@@]3([C@]41[C@@H]2[C@](O)(OC4)[C@@H]([C@]13CO1)O)O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3317744
PubChem CID:	n.a.
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
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	Activity	=	96.21	%	PMID[506662]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	102.0	%	PMID[506662]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	99.1	%	PMID[506662]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	101.0	%	PMID[506662]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	61.66	%	PMID[506662]

☑ 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 NPC102822 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	273
0.1-0.2	1636
0.2-0.3	4851
0.3-0.4	8086
0.4-0.5	11516
0.5-0.6	7529
0.6-0.7	5264
0.7-0.8	3009
0.8-0.85	410
0.85-0.9	85
0.9-0.95	33
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477046
0.973	High Similarity	NPC204552
0.973	High Similarity	NPC188667
0.964	High Similarity	NPC287343
0.964	High Similarity	NPC474654
0.964	High Similarity	NPC97908
0.964	High Similarity	NPC122033
0.964	High Similarity	NPC470854
0.9558	High Similarity	NPC112038
0.9469	High Similarity	NPC469488
0.9381	High Similarity	NPC17772
0.9381	High Similarity	NPC297179
0.9369	High Similarity	NPC7921
0.9369	High Similarity	NPC49451
0.9369	High Similarity	NPC208998
0.9279	High Similarity	NPC289312
0.9279	High Similarity	NPC11252
0.9211	High Similarity	NPC251310
0.9204	High Similarity	NPC40632
0.9204	High Similarity	NPC235539
0.9204	High Similarity	NPC134869
0.9204	High Similarity	NPC251236
0.9204	High Similarity	NPC152199
0.9204	High Similarity	NPC328374
0.9204	High Similarity	NPC96312
0.9189	High Similarity	NPC146945
0.9189	High Similarity	NPC171888
0.9189	High Similarity	NPC201992
0.913	High Similarity	NPC470777
0.9123	High Similarity	NPC470775
0.9123	High Similarity	NPC176513
0.9115	High Similarity	NPC474906
0.9115	High Similarity	NPC18547
0.9115	High Similarity	NPC473798
0.9035	High Similarity	NPC207217
0.9027	High Similarity	NPC51978
0.8992	High Similarity	NPC225049
0.8947	High Similarity	NPC143268
0.8947	High Similarity	NPC268238
0.8947	High Similarity	NPC45218
0.8947	High Similarity	NPC323821
0.8938	High Similarity	NPC474516
0.8919	High Similarity	NPC293850
0.8908	High Similarity	NPC470922
0.8908	High Similarity	NPC24651
0.8898	High Similarity	NPC312833
0.8879	High Similarity	NPC470776
0.887	High Similarity	NPC173686
0.887	High Similarity	NPC16081
0.8829	High Similarity	NPC144854
0.8829	High Similarity	NPC3316
0.8824	High Similarity	NPC18945
0.8824	High Similarity	NPC105926
0.8824	High Similarity	NPC265557
0.8824	High Similarity	NPC67251
0.8824	High Similarity	NPC91693
0.8803	High Similarity	NPC475775
0.8803	High Similarity	NPC476529
0.8783	High Similarity	NPC243354
0.878	High Similarity	NPC33378
0.878	High Similarity	NPC6274
0.878	High Similarity	NPC254146
0.8772	High Similarity	NPC302146
0.876	High Similarity	NPC470780
0.875	High Similarity	NPC154608
0.875	High Similarity	NPC277017
0.875	High Similarity	NPC192813
0.875	High Similarity	NPC476729
0.8729	High Similarity	NPC107338
0.8729	High Similarity	NPC109607
0.8707	High Similarity	NPC470628
0.8707	High Similarity	NPC474734
0.8707	High Similarity	NPC259306
0.8707	High Similarity	NPC179626
0.8707	High Similarity	NPC474046
0.8696	High Similarity	NPC194273
0.8696	High Similarity	NPC477266
0.8689	High Similarity	NPC188291
0.8684	High Similarity	NPC471243
0.8655	High Similarity	NPC470779
0.8632	High Similarity	NPC473590
0.8632	High Similarity	NPC27999
0.8632	High Similarity	NPC477116
0.8632	High Similarity	NPC309433
0.8629	High Similarity	NPC100390
0.8629	High Similarity	NPC254614
0.8621	High Similarity	NPC470919
0.8621	High Similarity	NPC469877
0.8609	High Similarity	NPC472002
0.8596	High Similarity	NPC474567
0.8571	High Similarity	NPC102352
0.8537	High Similarity	NPC475636
0.8537	High Similarity	NPC295220
0.8534	High Similarity	NPC320118
0.8525	High Similarity	NPC285091
0.8525	High Similarity	NPC87662
0.8512	High Similarity	NPC227397
0.8509	High Similarity	NPC143706
0.8509	High Similarity	NPC472534
0.8487	Intermediate Similarity	NPC268958
0.848	Intermediate Similarity	NPC102316
0.8475	Intermediate Similarity	NPC53396
0.8475	Intermediate Similarity	NPC13713
0.8475	Intermediate Similarity	NPC58662
0.8475	Intermediate Similarity	NPC98249
0.8475	Intermediate Similarity	NPC469684
0.8475	Intermediate Similarity	NPC473968
0.8468	Intermediate Similarity	NPC309096
0.8468	Intermediate Similarity	NPC264192
0.8468	Intermediate Similarity	NPC476851
0.8468	Intermediate Similarity	NPC54614
0.8462	Intermediate Similarity	NPC117712
0.8462	Intermediate Similarity	NPC247069
0.8455	Intermediate Similarity	NPC476008
0.8448	Intermediate Similarity	NPC473397
0.8443	Intermediate Similarity	NPC473255
0.8438	Intermediate Similarity	NPC596
0.8435	Intermediate Similarity	NPC210005
0.8435	Intermediate Similarity	NPC85391
0.843	Intermediate Similarity	NPC222688
0.843	Intermediate Similarity	NPC471965
0.8425	Intermediate Similarity	NPC262813
0.8413	Intermediate Similarity	NPC168879
0.8407	Intermediate Similarity	NPC181357
0.8403	Intermediate Similarity	NPC284707
0.84	Intermediate Similarity	NPC476852
0.8387	Intermediate Similarity	NPC476859
0.8387	Intermediate Similarity	NPC473620
0.8376	Intermediate Similarity	NPC477126
0.8376	Intermediate Similarity	NPC198539
0.8376	Intermediate Similarity	NPC471252
0.8376	Intermediate Similarity	NPC194100
0.8374	Intermediate Similarity	NPC477745
0.8374	Intermediate Similarity	NPC293112
0.8374	Intermediate Similarity	NPC473635
0.8374	Intermediate Similarity	NPC174367
0.8374	Intermediate Similarity	NPC217901
0.8374	Intermediate Similarity	NPC47113
0.8362	Intermediate Similarity	NPC474229
0.8362	Intermediate Similarity	NPC474846
0.8362	Intermediate Similarity	NPC469655
0.8362	Intermediate Similarity	NPC469656
0.8362	Intermediate Similarity	NPC29505
0.8362	Intermediate Similarity	NPC213320
0.8361	Intermediate Similarity	NPC202666
0.8361	Intermediate Similarity	NPC471961
0.8361	Intermediate Similarity	NPC43252
0.8361	Intermediate Similarity	NPC135038
0.8361	Intermediate Similarity	NPC11895
0.8361	Intermediate Similarity	NPC478066
0.8361	Intermediate Similarity	NPC262199
0.8361	Intermediate Similarity	NPC471964
0.8361	Intermediate Similarity	NPC14617
0.8359	Intermediate Similarity	NPC243014
0.8359	Intermediate Similarity	NPC471089
0.8359	Intermediate Similarity	NPC190065
0.8359	Intermediate Similarity	NPC141215
0.8359	Intermediate Similarity	NPC251998
0.8348	Intermediate Similarity	NPC474242
0.8348	Intermediate Similarity	NPC141350
0.8347	Intermediate Similarity	NPC275675
0.8347	Intermediate Similarity	NPC75417
0.8333	Intermediate Similarity	NPC319570
0.8333	Intermediate Similarity	NPC475139
0.8333	Intermediate Similarity	NPC473203
0.8333	Intermediate Similarity	NPC180902
0.832	Intermediate Similarity	NPC470880
0.832	Intermediate Similarity	NPC476854
0.8319	Intermediate Similarity	NPC65523
0.8319	Intermediate Similarity	NPC470778
0.8319	Intermediate Similarity	NPC146432
0.8319	Intermediate Similarity	NPC475036
0.8319	Intermediate Similarity	NPC470171
0.8306	Intermediate Similarity	NPC470882
0.8306	Intermediate Similarity	NPC475273
0.8306	Intermediate Similarity	NPC305496
0.8306	Intermediate Similarity	NPC168849
0.8306	Intermediate Similarity	NPC473253
0.8305	Intermediate Similarity	NPC299849
0.8295	Intermediate Similarity	NPC140045
0.8295	Intermediate Similarity	NPC295885
0.8293	Intermediate Similarity	NPC471963
0.8293	Intermediate Similarity	NPC177820
0.8293	Intermediate Similarity	NPC172154
0.8293	Intermediate Similarity	NPC30188
0.8293	Intermediate Similarity	NPC81736
0.8293	Intermediate Similarity	NPC470477
0.8293	Intermediate Similarity	NPC247315
0.8293	Intermediate Similarity	NPC471962
0.8291	Intermediate Similarity	NPC90769
0.8291	Intermediate Similarity	NPC205534
0.8291	Intermediate Similarity	NPC474927
0.8279	Intermediate Similarity	NPC170538
0.8279	Intermediate Similarity	NPC235438
0.8279	Intermediate Similarity	NPC107966
0.8279	Intermediate Similarity	NPC249848
0.8279	Intermediate Similarity	NPC65858
0.8279	Intermediate Similarity	NPC40775
0.8276	Intermediate Similarity	NPC320383
0.8276	Intermediate Similarity	NPC137104

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 NPC102822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	1857
0.2-0.3	3916
0.3-0.4	1988
0.4-0.5	605
0.5-0.6	307
0.6-0.7	155
0.7-0.8	86
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
0.8361	Intermediate Similarity	NPD8328	Phase 3
0.8115	Intermediate Similarity	NPD6319	Approved
0.8103	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7492	Approved
0.7967	Intermediate Similarity	NPD6059	Approved
0.7967	Intermediate Similarity	NPD6054	Approved
0.7953	Intermediate Similarity	NPD7736	Approved
0.7937	Intermediate Similarity	NPD6616	Approved
0.7903	Intermediate Similarity	NPD6015	Approved
0.7903	Intermediate Similarity	NPD6016	Approved
0.7881	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7078	Approved
0.7874	Intermediate Similarity	NPD8293	Discontinued
0.784	Intermediate Similarity	NPD5988	Approved
0.784	Intermediate Similarity	NPD6370	Approved
0.7815	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6008	Approved
0.7769	Intermediate Similarity	NPD4632	Approved
0.7752	Intermediate Similarity	NPD7319	Approved
0.7731	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD6372	Approved
0.7731	Intermediate Similarity	NPD6373	Approved
0.7724	Intermediate Similarity	NPD6009	Approved
0.7724	Intermediate Similarity	NPD7115	Discovery
0.7686	Intermediate Similarity	NPD6882	Approved
0.7686	Intermediate Similarity	NPD8297	Approved
0.7627	Intermediate Similarity	NPD5739	Approved
0.7627	Intermediate Similarity	NPD6675	Approved
0.7627	Intermediate Similarity	NPD7128	Approved
0.7627	Intermediate Similarity	NPD6402	Approved
0.7603	Intermediate Similarity	NPD6650	Approved
0.7603	Intermediate Similarity	NPD6649	Approved
0.7563	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5697	Approved
0.7563	Intermediate Similarity	NPD5701	Approved
0.7563	Intermediate Similarity	NPD6412	Phase 2
0.7521	Intermediate Similarity	NPD4634	Approved
0.7519	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.748	Intermediate Similarity	NPD6921	Approved
0.7438	Intermediate Similarity	NPD6014	Approved
0.7438	Intermediate Similarity	NPD6012	Approved
0.7438	Intermediate Similarity	NPD6013	Approved
0.7405	Intermediate Similarity	NPD6033	Approved
0.7377	Intermediate Similarity	NPD7290	Approved
0.7377	Intermediate Similarity	NPD7102	Approved
0.7377	Intermediate Similarity	NPD6883	Approved
0.7364	Intermediate Similarity	NPD7604	Phase 2
0.7355	Intermediate Similarity	NPD6011	Approved
0.7355	Intermediate Similarity	NPD6686	Approved
0.7344	Intermediate Similarity	NPD5983	Phase 2
0.7344	Intermediate Similarity	NPD8513	Phase 3
0.7344	Intermediate Similarity	NPD8516	Approved
0.7344	Intermediate Similarity	NPD8517	Approved
0.7344	Intermediate Similarity	NPD8515	Approved
0.7328	Intermediate Similarity	NPD4755	Approved
0.7323	Intermediate Similarity	NPD7516	Approved
0.7317	Intermediate Similarity	NPD8130	Phase 1
0.7317	Intermediate Similarity	NPD6617	Approved
0.7317	Intermediate Similarity	NPD6847	Approved
0.7317	Intermediate Similarity	NPD6869	Approved
0.7265	Intermediate Similarity	NPD4225	Approved
0.7244	Intermediate Similarity	NPD7328	Approved
0.7244	Intermediate Similarity	NPD7327	Approved
0.7203	Intermediate Similarity	NPD4700	Approved
0.7203	Intermediate Similarity	NPD4696	Approved
0.7203	Intermediate Similarity	NPD5285	Approved
0.7203	Intermediate Similarity	NPD5286	Approved
0.7179	Intermediate Similarity	NPD7902	Approved
0.7177	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6336	Discontinued
0.7094	Intermediate Similarity	NPD4697	Phase 3
0.7087	Intermediate Similarity	NPD6274	Approved
0.7083	Intermediate Similarity	NPD4633	Approved
0.7083	Intermediate Similarity	NPD5226	Approved
0.7083	Intermediate Similarity	NPD5211	Phase 2
0.7083	Intermediate Similarity	NPD5224	Approved
0.7083	Intermediate Similarity	NPD5225	Approved
0.7069	Intermediate Similarity	NPD5282	Discontinued
0.7069	Intermediate Similarity	NPD7748	Approved
0.7049	Intermediate Similarity	NPD4768	Approved
0.7049	Intermediate Similarity	NPD4767	Approved
0.7043	Intermediate Similarity	NPD7515	Phase 2
0.7034	Intermediate Similarity	NPD6084	Phase 2
0.7034	Intermediate Similarity	NPD6083	Phase 2
0.7025	Intermediate Similarity	NPD5175	Approved
0.7025	Intermediate Similarity	NPD5174	Approved
0.7	Intermediate Similarity	NPD5223	Approved
0.6991	Remote Similarity	NPD3573	Approved
0.6983	Remote Similarity	NPD6399	Phase 3
0.6975	Remote Similarity	NPD5696	Approved
0.6967	Remote Similarity	NPD5141	Approved
0.6949	Remote Similarity	NPD5221	Approved
0.6949	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5222	Approved
0.6947	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD8379	Approved
0.6947	Remote Similarity	NPD8296	Approved
0.6947	Remote Similarity	NPD8378	Approved
0.6947	Remote Similarity	NPD8033	Approved
0.6947	Remote Similarity	NPD8335	Approved
0.6947	Remote Similarity	NPD8380	Approved
0.694	Remote Similarity	NPD8074	Phase 3
0.6935	Remote Similarity	NPD4729	Approved
0.6935	Remote Similarity	NPD4730	Approved
0.6929	Remote Similarity	NPD8133	Approved
0.6923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7101	Approved
0.6923	Remote Similarity	NPD7100	Approved
0.6923	Remote Similarity	NPD7900	Approved
0.6905	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3618	Phase 1
0.6899	Remote Similarity	NPD6317	Approved
0.6897	Remote Similarity	NPD6411	Approved
0.6891	Remote Similarity	NPD5173	Approved
0.6885	Remote Similarity	NPD4754	Approved
0.687	Remote Similarity	NPD5328	Approved
0.687	Remote Similarity	NPD8294	Approved
0.687	Remote Similarity	NPD8377	Approved
0.6864	Remote Similarity	NPD5695	Phase 3
0.686	Remote Similarity	NPD1700	Approved
0.686	Remote Similarity	NPD5344	Discontinued
0.6846	Remote Similarity	NPD6313	Approved
0.6846	Remote Similarity	NPD6314	Approved
0.6846	Remote Similarity	NPD6335	Approved
0.6833	Remote Similarity	NPD7638	Approved
0.6825	Remote Similarity	NPD5248	Approved
0.6825	Remote Similarity	NPD5247	Approved
0.6825	Remote Similarity	NPD5251	Approved
0.6825	Remote Similarity	NPD5250	Approved
0.6825	Remote Similarity	NPD5249	Phase 3
0.6818	Remote Similarity	NPD7503	Approved
0.6818	Remote Similarity	NPD6909	Approved
0.6818	Remote Similarity	NPD6908	Approved
0.681	Remote Similarity	NPD46	Approved
0.681	Remote Similarity	NPD6698	Approved
0.68	Remote Similarity	NPD5128	Approved
0.6788	Remote Similarity	NPD5956	Approved
0.6777	Remote Similarity	NPD7639	Approved
0.6777	Remote Similarity	NPD7640	Approved
0.6752	Remote Similarity	NPD6079	Approved
0.6724	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6101	Approved
0.6724	Remote Similarity	NPD4753	Phase 2
0.6723	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6067	Discontinued
0.6695	Remote Similarity	NPD4202	Approved
0.6693	Remote Similarity	NPD6371	Approved
0.6692	Remote Similarity	NPD6868	Approved
0.6641	Remote Similarity	NPD5215	Approved
0.6641	Remote Similarity	NPD5216	Approved
0.6641	Remote Similarity	NPD5217	Approved
0.6638	Remote Similarity	NPD5737	Approved
0.6638	Remote Similarity	NPD6672	Approved
0.6619	Remote Similarity	NPD7260	Phase 2
0.6609	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5210	Approved
0.6583	Remote Similarity	NPD4629	Approved
0.6562	Remote Similarity	NPD5169	Approved
0.6562	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5135	Approved
0.6555	Remote Similarity	NPD5778	Approved
0.6555	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD3667	Approved
0.6512	Remote Similarity	NPD5127	Approved
0.6504	Remote Similarity	NPD6648	Approved
0.65	Remote Similarity	NPD6001	Approved
0.6496	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8034	Phase 2
0.6471	Remote Similarity	NPD8035	Phase 2
0.6471	Remote Similarity	NPD7983	Approved
0.6466	Remote Similarity	NPD7146	Approved
0.6466	Remote Similarity	NPD5330	Approved
0.6466	Remote Similarity	NPD7521	Approved
0.6466	Remote Similarity	NPD6684	Approved
0.6466	Remote Similarity	NPD7334	Approved
0.6466	Remote Similarity	NPD6409	Approved
0.6462	Remote Similarity	NPD6053	Discontinued
0.6458	Remote Similarity	NPD6334	Approved
0.6458	Remote Similarity	NPD6333	Approved
0.6454	Remote Similarity	NPD6845	Suspended
0.6441	Remote Similarity	NPD6904	Approved
0.6441	Remote Similarity	NPD6673	Approved
0.6441	Remote Similarity	NPD6080	Approved
0.6441	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4786	Approved
0.6435	Remote Similarity	NPD3133	Approved
0.6435	Remote Similarity	NPD3665	Phase 1
0.6435	Remote Similarity	NPD3666	Approved
0.6429	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD4522	Approved
0.6406	Remote Similarity	NPD5168	Approved
0.6397	Remote Similarity	NPD8080	Discontinued
0.6389	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD3168	Discontinued

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