NPASS Compound

Structure

CID3316 OpenBabel06191715322D 26 29 0 0 1 0 0 0 0 0999 V2000 -3.1368 0.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8160 -3.1873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3519 -2.3004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7841 -2.3004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9207 -0.4532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1366 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 -2.7163 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9205 -1.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3524 -0.4529 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -1.8107 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.7838 -3.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5684 -0.0002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5679 -2.7163 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5680 -1.8111 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1362 -1.8113 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7840 -0.4527 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7842 -1.3579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3522 -1.3584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7840 -1.3584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7455 -1.8353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7838 -4.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5683 0.9418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3837 -3.1873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1360 -2.7640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6941 -1.6016 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 6 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 2 1 1 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 8 20 2 0 0 0 0 9 12 1 0 0 0 0 9 18 1 6 0 0 0 10 17 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 6 0 0 0 12 16 1 0 0 0 0 12 22 1 1 0 0 0 13 14 1 0 0 0 0 13 23 1 6 0 0 0 14 18 1 6 0 0 0 14 19 1 0 0 0 0 15 18 1 6 0 0 0 15 24 1 0 0 0 0 16 19 1 1 0 0 0 16 26 1 0 0 0 0 17 25 2 0 0 0 0 17 26 1 0 0 0 0 18 3 1 6 0 0 0 19 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.17
Volume:	356.577
LogP:	0.547
LogD:	0.557
LogS:	-3.679
# Rotatable Bonds:	0
TPSA:	121.13
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.283
Fsp3:	0.842
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:	-5.119
MDCK Permeability:	8.32818477647379e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.38
Human Intestinal Absorption (HIA):	0.692
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	39.233787536621094%
Volume Distribution (VD):	0.42
Pgp-substrate:	48.34265899658203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.594
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	5.5
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.345
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.374
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.112
Carcinogencity:	0.031
Eye Corrosion:	0.009
Eye Irritation:	0.013
Respiratory Toxicity:	0.629

Download Data

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

Natural Product: NPC3316

Natural Product ID:	NPC3316
*Common Name:**	Longilactone
IUPAC Name:	n.a.
Synonyms:	Longilactone
Standard InCHIKey:	KBBRVTNGCNCUCX-GZKGTQTLSA-N
Standard InCHI:	InChI=1S/C19H26O7/c1-6-5-8(20)15(24)18(3)9(6)12(22)16-19(4)10(17(25)26-16)7(2)11(21)13(23)14(18)19/h5,7,9-16,21-24H,1-4H3/t7-,9-,10?,11+,12-,13+,14-,15-,16-,18+,19+/m1/s1
SMILES:	CC1=CC(=O)[C@H]([C@@]2(C)[C@H]1[C@H]([C@@H]1[C@@]3(C)C([C@@H](C)[C@@H]([C@@H]([C@H]23)O)O)C(=O)O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080174
PubChem CID:	46878941
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	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]
NPO20997	Eurycoma sp.	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
IC50	2
LD50	1
Others	7

Activity Type	# Activity
Cell Line	7
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	19000.0	nM	PMID[513980]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	99.66	%	PMID[513982]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	99.79	%	PMID[513982]
NPT81	Cell Line	A549	Homo sapiens	Activity	=	66.06	%	PMID[513982]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	101.0	%	PMID[513982]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	102.0	%	PMID[513982]
NPT165	Cell Line	HeLa	Homo sapiens	Activity	=	66.9	%	PMID[513982]
NPT140	Organism	Artemia	Artemia	LD50	=	144.8	ug ml-1	PMID[513981]
NPT2	Others	Unspecified		IC50	=	4700.0	nM	PMID[513981]
NPT2	Others	Unspecified		Inhibition	>	50.0	%	PMID[513981]

☑ 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 NPC3316 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	210
0.1-0.2	1221
0.2-0.3	4048
0.3-0.4	7620
0.4-0.5	12649
0.5-0.6	6487
0.6-0.7	5844
0.7-0.8	4092
0.8-0.85	393
0.85-0.9	98
0.9-0.95	28
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC144854
0.9899	High Similarity	NPC192813
0.9899	High Similarity	NPC277017
0.9899	High Similarity	NPC154608
0.9697	High Similarity	NPC102352
0.951	High Similarity	NPC210005
0.95	High Similarity	NPC181357
0.9423	High Similarity	NPC49451
0.9417	High Similarity	NPC201992
0.9412	High Similarity	NPC141350
0.9327	High Similarity	NPC11252
0.9327	High Similarity	NPC289312
0.9327	High Similarity	NPC474516
0.9314	High Similarity	NPC293850
0.9245	High Similarity	NPC96312
0.9245	High Similarity	NPC40632
0.9245	High Similarity	NPC251236
0.9245	High Similarity	NPC328374
0.9245	High Similarity	NPC207217
0.9238	High Similarity	NPC51978
0.9216	High Similarity	NPC230541
0.9159	High Similarity	NPC122033
0.9159	High Similarity	NPC97908
0.9159	High Similarity	NPC470854
0.9159	High Similarity	NPC287343
0.9159	High Similarity	NPC474654
0.9151	High Similarity	NPC474906
0.9151	High Similarity	NPC18547
0.9151	High Similarity	NPC473798
0.9074	High Similarity	NPC17772
0.9065	High Similarity	NPC152199
0.9065	High Similarity	NPC235539
0.9065	High Similarity	NPC134869
0.9048	High Similarity	NPC188738
0.8962	High Similarity	NPC472002
0.8922	High Similarity	NPC275583
0.8899	High Similarity	NPC188667
0.8899	High Similarity	NPC204552
0.8899	High Similarity	NPC297179
0.8889	High Similarity	NPC256227
0.8889	High Similarity	NPC179626
0.8879	High Similarity	NPC7921
0.8879	High Similarity	NPC208998
0.8868	High Similarity	NPC171888
0.8868	High Similarity	NPC146945
0.8857	High Similarity	NPC27814
0.8829	High Similarity	NPC477046
0.8829	High Similarity	NPC102822
0.8818	High Similarity	NPC476529
0.8818	High Similarity	NPC470777
0.8818	High Similarity	NPC475775
0.8812	High Similarity	NPC472972
0.8785	High Similarity	NPC302146
0.8762	High Similarity	NPC19412
0.8739	High Similarity	NPC112038
0.8739	High Similarity	NPC109607
0.8739	High Similarity	NPC107338
0.8738	High Similarity	NPC264048
0.8727	High Similarity	NPC251310
0.8716	High Similarity	NPC478216
0.8716	High Similarity	NPC474734
0.8704	High Similarity	NPC194100
0.8679	High Similarity	NPC472534
0.8679	High Similarity	NPC153239
0.8679	High Similarity	NPC310546
0.8679	High Similarity	NPC143706
0.8654	High Similarity	NPC65523
0.8649	High Similarity	NPC469488
0.8636	High Similarity	NPC176513
0.8636	High Similarity	NPC470775
0.8636	High Similarity	NPC309433
0.8636	High Similarity	NPC473590
0.8624	High Similarity	NPC117712
0.8624	High Similarity	NPC323821
0.8624	High Similarity	NPC470919
0.8624	High Similarity	NPC143268
0.8624	High Similarity	NPC243354
0.8624	High Similarity	NPC469877
0.8624	High Similarity	NPC45218
0.8624	High Similarity	NPC268238
0.8611	High Similarity	NPC280782
0.8598	High Similarity	NPC5103
0.8596	High Similarity	NPC24651
0.8585	High Similarity	NPC275539
0.8585	High Similarity	NPC189075
0.8584	High Similarity	NPC312833
0.8584	High Similarity	NPC222688
0.8571	High Similarity	NPC469607
0.8571	High Similarity	NPC109973
0.8571	High Similarity	NPC96377
0.8559	High Similarity	NPC470776
0.8545	High Similarity	NPC49492
0.8545	High Similarity	NPC259306
0.8545	High Similarity	NPC470628
0.8545	High Similarity	NPC173686
0.8545	High Similarity	NPC474046
0.8545	High Similarity	NPC16081
0.8545	High Similarity	NPC266728
0.8532	High Similarity	NPC962
0.8532	High Similarity	NPC194273
0.8532	High Similarity	NPC250109
0.8519	High Similarity	NPC469656
0.8519	High Similarity	NPC100329
0.8519	High Similarity	NPC471243
0.8519	High Similarity	NPC474846
0.8519	High Similarity	NPC132790
0.8519	High Similarity	NPC97939
0.8519	High Similarity	NPC247031
0.8519	High Similarity	NPC469655
0.8509	High Similarity	NPC91693
0.8509	High Similarity	NPC18945
0.8509	High Similarity	NPC265557
0.8509	High Similarity	NPC105926
0.8509	High Similarity	NPC67251
0.8505	High Similarity	NPC478210
0.8491	Intermediate Similarity	NPC202524
0.8491	Intermediate Similarity	NPC59530
0.8491	Intermediate Similarity	NPC110496
0.8482	Intermediate Similarity	NPC475041
0.8476	Intermediate Similarity	NPC258532
0.8476	Intermediate Similarity	NPC471293
0.8476	Intermediate Similarity	NPC255309
0.8468	Intermediate Similarity	NPC98249
0.8468	Intermediate Similarity	NPC473968
0.8468	Intermediate Similarity	NPC53396
0.8468	Intermediate Similarity	NPC284068
0.8455	Intermediate Similarity	NPC247069
0.844	Intermediate Similarity	NPC234042
0.844	Intermediate Similarity	NPC90769
0.844	Intermediate Similarity	NPC71348
0.844	Intermediate Similarity	NPC152117
0.844	Intermediate Similarity	NPC269530
0.8435	Intermediate Similarity	NPC476729
0.8435	Intermediate Similarity	NPC470922
0.8426	Intermediate Similarity	NPC478211
0.8426	Intermediate Similarity	NPC239097
0.8426	Intermediate Similarity	NPC253906
0.8426	Intermediate Similarity	NPC5284
0.8426	Intermediate Similarity	NPC286880
0.8426	Intermediate Similarity	NPC474567
0.8411	Intermediate Similarity	NPC94529
0.8411	Intermediate Similarity	NPC94942
0.8393	Intermediate Similarity	NPC284707
0.8381	Intermediate Similarity	NPC209298
0.8381	Intermediate Similarity	NPC159442
0.8381	Intermediate Similarity	NPC277074
0.8381	Intermediate Similarity	NPC140723
0.8381	Intermediate Similarity	NPC95585
0.8381	Intermediate Similarity	NPC282233
0.8378	Intermediate Similarity	NPC270958
0.8365	Intermediate Similarity	NPC81530
0.8365	Intermediate Similarity	NPC97435
0.8365	Intermediate Similarity	NPC252614
0.8364	Intermediate Similarity	NPC198539
0.8364	Intermediate Similarity	NPC475966
0.8364	Intermediate Similarity	NPC469463
0.8364	Intermediate Similarity	NPC469454
0.8364	Intermediate Similarity	NPC202889
0.8364	Intermediate Similarity	NPC469496
0.835	Intermediate Similarity	NPC114274
0.8349	Intermediate Similarity	NPC179798
0.8349	Intermediate Similarity	NPC304180
0.8333	Intermediate Similarity	NPC470779
0.8319	Intermediate Similarity	NPC268958
0.8318	Intermediate Similarity	NPC293512
0.8304	Intermediate Similarity	NPC477116
0.8304	Intermediate Similarity	NPC13713
0.8304	Intermediate Similarity	NPC58662
0.8304	Intermediate Similarity	NPC469684
0.8304	Intermediate Similarity	NPC27999
0.8302	Intermediate Similarity	NPC475036
0.8302	Intermediate Similarity	NPC96268
0.8302	Intermediate Similarity	NPC284865
0.8302	Intermediate Similarity	NPC29705
0.8302	Intermediate Similarity	NPC301787
0.8288	Intermediate Similarity	NPC326542
0.8286	Intermediate Similarity	NPC136289
0.8286	Intermediate Similarity	NPC273005
0.8286	Intermediate Similarity	NPC31058
0.8286	Intermediate Similarity	NPC295791
0.8286	Intermediate Similarity	NPC469606
0.8276	Intermediate Similarity	NPC473255
0.8273	Intermediate Similarity	NPC207251
0.8273	Intermediate Similarity	NPC194951
0.8273	Intermediate Similarity	NPC12046
0.8273	Intermediate Similarity	NPC205534
0.8269	Intermediate Similarity	NPC316964
0.8269	Intermediate Similarity	NPC470388
0.8261	Intermediate Similarity	NPC269642
0.8257	Intermediate Similarity	NPC197428
0.8252	Intermediate Similarity	NPC43686
0.8246	Intermediate Similarity	NPC478051
0.8241	Intermediate Similarity	NPC273155
0.8241	Intermediate Similarity	NPC476479
0.823	Intermediate Similarity	NPC106644
0.823	Intermediate Similarity	NPC118638
0.8224	Intermediate Similarity	NPC278628
0.8224	Intermediate Similarity	NPC231530
0.8224	Intermediate Similarity	NPC478208
0.8224	Intermediate Similarity	NPC222833

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 NPC3316 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1496
0.2-0.3	3749
0.3-0.4	2356
0.4-0.5	822
0.5-0.6	248
0.6-0.7	138
0.7-0.8	124
0.8-0.85	37
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8532	High Similarity	NPD4632	Approved
0.8246	Intermediate Similarity	NPD6319	Approved
0.8224	Intermediate Similarity	NPD7128	Approved
0.8224	Intermediate Similarity	NPD6675	Approved
0.8224	Intermediate Similarity	NPD6008	Approved
0.8224	Intermediate Similarity	NPD5739	Approved
0.8224	Intermediate Similarity	NPD6402	Approved
0.8165	Intermediate Similarity	NPD6372	Approved
0.8165	Intermediate Similarity	NPD6373	Approved
0.8148	Intermediate Similarity	NPD5697	Approved
0.8148	Intermediate Similarity	NPD5701	Approved
0.8142	Intermediate Similarity	NPD6009	Approved
0.8108	Intermediate Similarity	NPD8297	Approved
0.8073	Intermediate Similarity	NPD7320	Approved
0.8073	Intermediate Similarity	NPD6899	Approved
0.8073	Intermediate Similarity	NPD6881	Approved
0.8073	Intermediate Similarity	NPD6011	Approved
0.8034	Intermediate Similarity	NPD8328	Phase 3
0.8018	Intermediate Similarity	NPD6650	Approved
0.8018	Intermediate Similarity	NPD6649	Approved
0.8017	Intermediate Similarity	NPD5983	Phase 2
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.7981	Intermediate Similarity	NPD4697	Phase 3
0.7966	Intermediate Similarity	NPD7492	Approved
0.7931	Intermediate Similarity	NPD6054	Approved
0.7931	Intermediate Similarity	NPD6059	Approved
0.7928	Intermediate Similarity	NPD6883	Approved
0.7928	Intermediate Similarity	NPD7290	Approved
0.7928	Intermediate Similarity	NPD7102	Approved
0.7909	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD7902	Approved
0.7905	Intermediate Similarity	NPD4755	Approved
0.7899	Intermediate Similarity	NPD6616	Approved
0.7881	Intermediate Similarity	NPD7604	Phase 2
0.7864	Intermediate Similarity	NPD6399	Phase 3
0.7863	Intermediate Similarity	NPD6015	Approved
0.7863	Intermediate Similarity	NPD6016	Approved
0.7857	Intermediate Similarity	NPD8130	Phase 1
0.7857	Intermediate Similarity	NPD6617	Approved
0.7857	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6869	Approved
0.7857	Intermediate Similarity	NPD6847	Approved
0.7838	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD7078	Approved
0.7833	Intermediate Similarity	NPD8293	Discontinued
0.781	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD5221	Approved
0.781	Intermediate Similarity	NPD5222	Approved
0.78	Intermediate Similarity	NPD3618	Phase 1
0.7797	Intermediate Similarity	NPD5988	Approved
0.7797	Intermediate Similarity	NPD6370	Approved
0.7788	Intermediate Similarity	NPD6882	Approved
0.7788	Intermediate Similarity	NPD7748	Approved
0.7769	Intermediate Similarity	NPD7736	Approved
0.7768	Intermediate Similarity	NPD4634	Approved
0.7767	Intermediate Similarity	NPD7515	Phase 2
0.7757	Intermediate Similarity	NPD5286	Approved
0.7757	Intermediate Similarity	NPD4700	Approved
0.7757	Intermediate Similarity	NPD4696	Approved
0.7757	Intermediate Similarity	NPD5285	Approved
0.775	Intermediate Similarity	NPD6336	Discontinued
0.7745	Intermediate Similarity	NPD5328	Approved
0.7736	Intermediate Similarity	NPD5173	Approved
0.7685	Intermediate Similarity	NPD5223	Approved
0.7679	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD7638	Approved
0.7664	Intermediate Similarity	NPD4225	Approved
0.7658	Intermediate Similarity	NPD6412	Phase 2
0.7619	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7900	Approved
0.7615	Intermediate Similarity	NPD5224	Approved
0.7615	Intermediate Similarity	NPD5211	Phase 2
0.7615	Intermediate Similarity	NPD4633	Approved
0.7615	Intermediate Similarity	NPD5226	Approved
0.7615	Intermediate Similarity	NPD5225	Approved
0.7611	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6079	Approved
0.7593	Intermediate Similarity	NPD7639	Approved
0.7593	Intermediate Similarity	NPD7640	Approved
0.7586	Intermediate Similarity	NPD6274	Approved
0.757	Intermediate Similarity	NPD6083	Phase 2
0.757	Intermediate Similarity	NPD6084	Phase 2
0.7563	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD4754	Approved
0.7545	Intermediate Similarity	NPD5174	Approved
0.7545	Intermediate Similarity	NPD5175	Approved
0.7521	Intermediate Similarity	NPD7115	Discovery
0.7521	Intermediate Similarity	NPD6317	Approved
0.75	Intermediate Similarity	NPD5696	Approved
0.748	Intermediate Similarity	NPD6033	Approved
0.7477	Intermediate Similarity	NPD5141	Approved
0.7476	Intermediate Similarity	NPD5737	Approved
0.7476	Intermediate Similarity	NPD6672	Approved
0.7458	Intermediate Similarity	NPD6335	Approved
0.7458	Intermediate Similarity	NPD6313	Approved
0.7458	Intermediate Similarity	NPD6314	Approved
0.7436	Intermediate Similarity	NPD6868	Approved
0.7434	Intermediate Similarity	NPD6686	Approved
0.7411	Intermediate Similarity	NPD4768	Approved
0.7411	Intermediate Similarity	NPD4767	Approved
0.74	Intermediate Similarity	NPD3667	Approved
0.7395	Intermediate Similarity	NPD7101	Approved
0.7395	Intermediate Similarity	NPD7100	Approved
0.7383	Intermediate Similarity	NPD5695	Phase 3
0.7379	Intermediate Similarity	NPD3573	Approved
0.7358	Intermediate Similarity	NPD4202	Approved
0.7345	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7507	Approved
0.7282	Intermediate Similarity	NPD7146	Approved
0.7282	Intermediate Similarity	NPD6409	Approved
0.7282	Intermediate Similarity	NPD5330	Approved
0.7282	Intermediate Similarity	NPD7521	Approved
0.7282	Intermediate Similarity	NPD7334	Approved
0.7282	Intermediate Similarity	NPD6684	Approved
0.7281	Intermediate Similarity	NPD5128	Approved
0.7281	Intermediate Similarity	NPD4730	Approved
0.7281	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD6908	Approved
0.7273	Intermediate Similarity	NPD6909	Approved
0.7255	Intermediate Similarity	NPD3666	Approved
0.7255	Intermediate Similarity	NPD3133	Approved
0.7255	Intermediate Similarity	NPD4786	Approved
0.7255	Intermediate Similarity	NPD3665	Phase 1
0.7238	Intermediate Similarity	NPD4753	Phase 2
0.7222	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4695	Discontinued
0.7155	Intermediate Similarity	NPD5135	Approved
0.7155	Intermediate Similarity	NPD5249	Phase 3
0.7155	Intermediate Similarity	NPD5169	Approved
0.7155	Intermediate Similarity	NPD5251	Approved
0.7155	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5248	Approved
0.7155	Intermediate Similarity	NPD5247	Approved
0.7155	Intermediate Similarity	NPD5250	Approved
0.7154	Intermediate Similarity	NPD6067	Discontinued
0.7143	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD6921	Approved
0.713	Intermediate Similarity	NPD5282	Discontinued
0.713	Intermediate Similarity	NPD5168	Approved
0.7115	Intermediate Similarity	NPD5279	Phase 3
0.7103	Intermediate Similarity	NPD6411	Approved
0.7103	Intermediate Similarity	NPD8034	Phase 2
0.7103	Intermediate Similarity	NPD8035	Phase 2
0.7094	Intermediate Similarity	NPD5215	Approved
0.7094	Intermediate Similarity	NPD5217	Approved
0.7094	Intermediate Similarity	NPD5127	Approved
0.7094	Intermediate Similarity	NPD5216	Approved
0.7075	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6904	Approved
0.7075	Intermediate Similarity	NPD6673	Approved
0.7075	Intermediate Similarity	NPD6080	Approved
0.7064	Intermediate Similarity	NPD4629	Approved
0.7064	Intermediate Similarity	NPD5210	Approved
0.7031	Intermediate Similarity	NPD7260	Phase 2
0.7019	Intermediate Similarity	NPD1694	Approved
0.6991	Remote Similarity	NPD7632	Discontinued
0.6972	Remote Similarity	NPD6001	Approved
0.6952	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5281	Approved
0.6944	Remote Similarity	NPD5284	Approved
0.6944	Remote Similarity	NPD5693	Phase 1
0.6923	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD3668	Phase 3
0.6917	Remote Similarity	NPD5167	Approved
0.6916	Remote Similarity	NPD6101	Approved
0.6916	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6053	Discontinued
0.6881	Remote Similarity	NPD5778	Approved
0.6881	Remote Similarity	NPD5779	Approved
0.6857	Remote Similarity	NPD5329	Approved
0.6857	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8515	Approved
0.6855	Remote Similarity	NPD8516	Approved
0.6855	Remote Similarity	NPD8517	Approved
0.6855	Remote Similarity	NPD8513	Phase 3
0.6852	Remote Similarity	NPD6698	Approved
0.6852	Remote Similarity	NPD5692	Phase 3
0.6852	Remote Similarity	NPD46	Approved
0.6846	Remote Similarity	NPD6845	Suspended
0.6842	Remote Similarity	NPD6334	Approved
0.6842	Remote Similarity	NPD6333	Approved
0.6832	Remote Similarity	NPD3617	Approved
0.6829	Remote Similarity	NPD7516	Approved
0.6792	Remote Similarity	NPD6098	Approved
0.6789	Remote Similarity	NPD5694	Approved
0.6789	Remote Similarity	NPD6050	Approved
0.6754	Remote Similarity	NPD5344	Discontinued
0.6752	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7327	Approved
0.6748	Remote Similarity	NPD7328	Approved
0.6731	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4221	Approved
0.6731	Remote Similarity	NPD4223	Phase 3
0.6723	Remote Similarity	NPD6371	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