NPASS Compound

Structure

CID293850 OpenBabel06191716102D 28 31 0 0 1 0 0 0 0 0999 V2000 3.3347 -1.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 2.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 2.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2007 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6026 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9955 3.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3347 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 2.7272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4686 0.2272 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2007 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 0.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1294 1.7272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7366 3.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6945 1.2029 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6026 2.7272 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6026 1.7272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3347 1.7272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6369 0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 1.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7366 1.2272 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8615 2.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0667 1.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7366 4.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6254 1.5682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 3.2272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3347 2.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 -0.0658 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 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 21 1 0 0 0 0 7 9 1 0 0 0 0 8 6 1 1 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 19 1 6 0 0 0 10 17 1 0 0 0 0 10 22 2 0 0 0 0 11 20 1 1 0 0 0 11 28 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 1 0 0 0 13 15 1 0 0 0 0 13 23 1 1 0 0 0 14 18 1 0 0 0 0 14 24 1 6 0 0 0 15 16 1 0 0 0 0 15 25 1 6 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 19 1 6 0 0 0 17 26 1 0 0 0 0 18 27 2 0 0 0 0 18 28 1 0 0 0 0 19 2 1 6 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.18
Volume:	382.663
LogP:	0.083
LogD:	0.08
LogS:	-2.979
# Rotatable Bonds:	1
TPSA:	141.36
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.329
Synthetic Accessibility Score:	5.385
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:	-5.587
MDCK Permeability:	0.00010987859423039481
Pgp-inhibitor:	0.555
Pgp-substrate:	0.862
Human Intestinal Absorption (HIA):	0.75
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.67

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.317
Plasma Protein Binding (PPB):	23.668926239013672%
Volume Distribution (VD):	0.353
Pgp-substrate:	64.44719696044922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.168
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.686
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	3.611
Half-life (T1/2):	0.451

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.228
Drug-inuced Liver Injury (DILI):	0.307
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.232
Maximum Recommended Daily Dose:	0.017
Skin Sensitization:	0.088
Carcinogencity:	0.039
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.26

Download Data

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

Natural Product: NPC293850

Natural Product ID:	NPC293850
*Common Name:**	AFJYIZMCHVBLPP-YREBFMARSA-N
IUPAC Name:	n.a.
Synonyms:	Rel-Yadanziolide T
Standard InCHIKey:	AFJYIZMCHVBLPP-YREBFMARSA-N
Standard InCHI:	InChI=1S/C20H28O8/c1-7-4-10(22)17(26)19(2)9(7)5-11-20(3)12(14(24)18(27)28-11)8(6-21)13(23)15(25)16(19)20/h4,8-9,11-17,21,23-26H,5-6H2,1-3H3/t8-,9+,11-,12-,13-,14-,15+,16-,17-,19+,20+/m1/s1
SMILES:	OC[C@H]1[C@@H](O)[C@H](O)[C@H]2[C@@]3([C@H]1[C@@H](O)C(=O)O[C@@H]3C[C@@H]1[C@]2(C)[C@H](O)C(=O)C=C1C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923102
PubChem CID:	56833962
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
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[22070654]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[22070654]
NPO15436	Brucea mollis	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[24199564]
NPO15436	Brucea mollis	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	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	3360.0	nM	PMID[523111]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	4400.0	nM	PMID[523111]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[523111]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[523111]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3000.0	nM	PMID[523111]

☑ 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 NPC293850 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	243
0.1-0.2	1436
0.2-0.3	4179
0.3-0.4	7428
0.4-0.5	12598
0.5-0.6	7565
0.6-0.7	5332
0.7-0.8	3151
0.8-0.85	637
0.85-0.9	85
0.9-0.95	40
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9612	High Similarity	NPC11252
0.9612	High Similarity	NPC289312
0.9519	High Similarity	NPC208998
0.9519	High Similarity	NPC7921
0.9519	High Similarity	NPC49451
0.9515	High Similarity	NPC201992
0.9429	High Similarity	NPC18547
0.9429	High Similarity	NPC474906
0.934	High Similarity	NPC235539
0.934	High Similarity	NPC328374
0.934	High Similarity	NPC96312
0.934	High Similarity	NPC134869
0.934	High Similarity	NPC40632
0.934	High Similarity	NPC152199
0.934	High Similarity	NPC251236
0.9333	High Similarity	NPC51978
0.9327	High Similarity	NPC171888
0.9327	High Similarity	NPC146945
0.9314	High Similarity	NPC144854
0.9314	High Similarity	NPC3316
0.9252	High Similarity	NPC470854
0.9252	High Similarity	NPC474654
0.9252	High Similarity	NPC309433
0.9252	High Similarity	NPC287343
0.9252	High Similarity	NPC97908
0.9252	High Similarity	NPC122033
0.9245	High Similarity	NPC473798
0.9238	High Similarity	NPC474516
0.9223	High Similarity	NPC192813
0.9223	High Similarity	NPC154608
0.9223	High Similarity	NPC277017
0.9167	High Similarity	NPC204552
0.9167	High Similarity	NPC17772
0.9167	High Similarity	NPC251310
0.9167	High Similarity	NPC188667
0.9167	High Similarity	NPC297179
0.9083	High Similarity	NPC475775
0.9083	High Similarity	NPC476529
0.9057	High Similarity	NPC302146
0.9029	High Similarity	NPC102352
0.902	High Similarity	NPC275583
0.9	High Similarity	NPC107338
0.9	High Similarity	NPC112038
0.9	High Similarity	NPC109607
0.8972	High Similarity	NPC194100
0.8952	High Similarity	NPC27814
0.8919	High Similarity	NPC102822
0.8919	High Similarity	NPC477046
0.8911	High Similarity	NPC472972
0.8909	High Similarity	NPC469488
0.8909	High Similarity	NPC470777
0.8889	High Similarity	NPC469877
0.8889	High Similarity	NPC470919
0.8868	High Similarity	NPC210005
0.8846	High Similarity	NPC181357
0.8807	High Similarity	NPC207217
0.8807	High Similarity	NPC470628
0.8807	High Similarity	NPC474046
0.8807	High Similarity	NPC474734
0.8807	High Similarity	NPC259306
0.8774	High Similarity	NPC141350
0.8774	High Similarity	NPC143706
0.8774	High Similarity	NPC310546
0.8774	High Similarity	NPC472534
0.875	High Similarity	NPC475036
0.875	High Similarity	NPC65523
0.8727	High Similarity	NPC473968
0.8727	High Similarity	NPC473590
0.8727	High Similarity	NPC176513
0.8727	High Similarity	NPC470775
0.8716	High Similarity	NPC102088
0.8716	High Similarity	NPC243354
0.8716	High Similarity	NPC268238
0.8716	High Similarity	NPC143268
0.8716	High Similarity	NPC323821
0.8716	High Similarity	NPC45218
0.8704	High Similarity	NPC90769
0.8684	High Similarity	NPC24651
0.8684	High Similarity	NPC470922
0.8673	High Similarity	NPC312833
0.8649	High Similarity	NPC470776
0.8636	High Similarity	NPC173686
0.8636	High Similarity	NPC16081
0.8624	High Similarity	NPC62696
0.8624	High Similarity	NPC293038
0.8624	High Similarity	NPC194273
0.8611	High Similarity	NPC471243
0.8596	High Similarity	NPC265557
0.8596	High Similarity	NPC67251
0.8596	High Similarity	NPC105926
0.8596	High Similarity	NPC18945
0.8596	High Similarity	NPC91693
0.8585	High Similarity	NPC230541
0.8585	High Similarity	NPC202524
0.8571	High Similarity	NPC127530
0.8571	High Similarity	NPC473401
0.8545	High Similarity	NPC475633
0.8532	High Similarity	NPC471967
0.8532	High Similarity	NPC472002
0.8532	High Similarity	NPC280782
0.8522	High Similarity	NPC476729
0.8522	High Similarity	NPC473255
0.8509	High Similarity	NPC471965
0.8505	High Similarity	NPC94942
0.8505	High Similarity	NPC272576
0.8491	Intermediate Similarity	NPC477877
0.8468	Intermediate Similarity	NPC179626
0.8462	Intermediate Similarity	NPC476132
0.8455	Intermediate Similarity	NPC255017
0.8455	Intermediate Similarity	NPC320118
0.8455	Intermediate Similarity	NPC198539
0.844	Intermediate Similarity	NPC188738
0.844	Intermediate Similarity	NPC34315
0.8435	Intermediate Similarity	NPC14617
0.8435	Intermediate Similarity	NPC262199
0.8435	Intermediate Similarity	NPC202666
0.8435	Intermediate Similarity	NPC471961
0.8435	Intermediate Similarity	NPC471964
0.8426	Intermediate Similarity	NPC41405
0.8421	Intermediate Similarity	NPC275675
0.8421	Intermediate Similarity	NPC470779
0.8407	Intermediate Similarity	NPC77689
0.8407	Intermediate Similarity	NPC473636
0.8393	Intermediate Similarity	NPC134430
0.8378	Intermediate Similarity	NPC178289
0.8376	Intermediate Similarity	NPC470882
0.8365	Intermediate Similarity	NPC476195
0.8364	Intermediate Similarity	NPC116794
0.8364	Intermediate Similarity	NPC234042
0.8364	Intermediate Similarity	NPC152117
0.8362	Intermediate Similarity	NPC471963
0.8362	Intermediate Similarity	NPC247315
0.8362	Intermediate Similarity	NPC471962
0.8349	Intermediate Similarity	NPC68419
0.8349	Intermediate Similarity	NPC102914
0.8349	Intermediate Similarity	NPC7870
0.8349	Intermediate Similarity	NPC220984
0.8349	Intermediate Similarity	NPC108709
0.8349	Intermediate Similarity	NPC110139
0.8349	Intermediate Similarity	NPC75747
0.8349	Intermediate Similarity	NPC274507
0.8349	Intermediate Similarity	NPC199457
0.8348	Intermediate Similarity	NPC222688
0.8333	Intermediate Similarity	NPC471406
0.8333	Intermediate Similarity	NPC476479
0.8333	Intermediate Similarity	NPC477437
0.8333	Intermediate Similarity	NPC477438
0.8333	Intermediate Similarity	NPC94529
0.8319	Intermediate Similarity	NPC286347
0.8317	Intermediate Similarity	NPC477436
0.8317	Intermediate Similarity	NPC477435
0.8302	Intermediate Similarity	NPC282233
0.8302	Intermediate Similarity	NPC95585
0.8302	Intermediate Similarity	NPC264048
0.8291	Intermediate Similarity	NPC285091
0.8288	Intermediate Similarity	NPC962
0.8288	Intermediate Similarity	NPC471204
0.8288	Intermediate Similarity	NPC477266
0.8288	Intermediate Similarity	NPC250109
0.8288	Intermediate Similarity	NPC271138
0.8288	Intermediate Similarity	NPC269315
0.8276	Intermediate Similarity	NPC227397
0.8273	Intermediate Similarity	NPC250481
0.8273	Intermediate Similarity	NPC297208
0.8273	Intermediate Similarity	NPC213320
0.8273	Intermediate Similarity	NPC179434
0.8273	Intermediate Similarity	NPC108748
0.8273	Intermediate Similarity	NPC30397
0.8273	Intermediate Similarity	NPC263827
0.8273	Intermediate Similarity	NPC211798
0.8273	Intermediate Similarity	NPC191763
0.8273	Intermediate Similarity	NPC473481
0.8273	Intermediate Similarity	NPC235841
0.8273	Intermediate Similarity	NPC285410
0.8269	Intermediate Similarity	NPC58942
0.8269	Intermediate Similarity	NPC260149
0.8261	Intermediate Similarity	NPC202051
0.8261	Intermediate Similarity	NPC470921
0.8261	Intermediate Similarity	NPC75417
0.8257	Intermediate Similarity	NPC137917
0.8257	Intermediate Similarity	NPC167383
0.8257	Intermediate Similarity	NPC237503
0.8257	Intermediate Similarity	NPC306746
0.8257	Intermediate Similarity	NPC204407
0.8257	Intermediate Similarity	NPC127853
0.8257	Intermediate Similarity	NPC57362
0.8252	Intermediate Similarity	NPC19376
0.8252	Intermediate Similarity	NPC469528
0.8252	Intermediate Similarity	NPC476318
0.8252	Intermediate Similarity	NPC469369
0.8252	Intermediate Similarity	NPC476327
0.8252	Intermediate Similarity	NPC256227
0.8252	Intermediate Similarity	NPC307282
0.8252	Intermediate Similarity	NPC305464
0.8252	Intermediate Similarity	NPC25848
0.825	Intermediate Similarity	NPC471855
0.8246	Intermediate Similarity	NPC6377
0.8246	Intermediate Similarity	NPC472949
0.8246	Intermediate Similarity	NPC475041
0.8246	Intermediate Similarity	NPC473839

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 NPC293850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	1723
0.2-0.3	3643
0.3-0.4	2220
0.4-0.5	805
0.5-0.6	280
0.6-0.7	138
0.7-0.8	112
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8435	Intermediate Similarity	NPD8328	Phase 3
0.8333	Intermediate Similarity	NPD6319	Approved
0.8288	Intermediate Similarity	NPD4632	Approved
0.8198	Intermediate Similarity	NPD8297	Approved
0.8148	Intermediate Similarity	NPD6675	Approved
0.8148	Intermediate Similarity	NPD7128	Approved
0.8148	Intermediate Similarity	NPD6402	Approved
0.8148	Intermediate Similarity	NPD5739	Approved
0.8091	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD6372	Approved
0.8091	Intermediate Similarity	NPD6373	Approved
0.8073	Intermediate Similarity	NPD5701	Approved
0.8073	Intermediate Similarity	NPD5697	Approved
0.807	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6899	Approved
0.8	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6881	Approved
0.8	Intermediate Similarity	NPD7320	Approved
0.7946	Intermediate Similarity	NPD6649	Approved
0.7946	Intermediate Similarity	NPD6650	Approved
0.7928	Intermediate Similarity	NPD6013	Approved
0.7928	Intermediate Similarity	NPD6014	Approved
0.7928	Intermediate Similarity	NPD6012	Approved
0.7913	Intermediate Similarity	NPD6009	Approved
0.7909	Intermediate Similarity	NPD6412	Phase 2
0.7885	Intermediate Similarity	NPD7748	Approved
0.7876	Intermediate Similarity	NPD6882	Approved
0.7864	Intermediate Similarity	NPD7515	Phase 2
0.7857	Intermediate Similarity	NPD6883	Approved
0.7857	Intermediate Similarity	NPD7102	Approved
0.7857	Intermediate Similarity	NPD7290	Approved
0.7838	Intermediate Similarity	NPD6011	Approved
0.783	Intermediate Similarity	NPD4755	Approved
0.783	Intermediate Similarity	NPD7902	Approved
0.7797	Intermediate Similarity	NPD5983	Phase 2
0.7788	Intermediate Similarity	NPD6617	Approved
0.7788	Intermediate Similarity	NPD8130	Phase 1
0.7788	Intermediate Similarity	NPD6847	Approved
0.7788	Intermediate Similarity	NPD6869	Approved
0.7768	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7492	Approved
0.7712	Intermediate Similarity	NPD6054	Approved
0.7712	Intermediate Similarity	NPD6059	Approved
0.7705	Intermediate Similarity	NPD7736	Approved
0.7699	Intermediate Similarity	NPD4634	Approved
0.7686	Intermediate Similarity	NPD7507	Approved
0.7686	Intermediate Similarity	NPD6616	Approved
0.7685	Intermediate Similarity	NPD4700	Approved
0.7685	Intermediate Similarity	NPD4696	Approved
0.7685	Intermediate Similarity	NPD5286	Approved
0.7685	Intermediate Similarity	NPD5285	Approved
0.7679	Intermediate Similarity	NPD6686	Approved
0.7667	Intermediate Similarity	NPD7604	Phase 2
0.7658	Intermediate Similarity	NPD6008	Approved
0.7647	Intermediate Similarity	NPD6015	Approved
0.7647	Intermediate Similarity	NPD3573	Approved
0.7647	Intermediate Similarity	NPD6016	Approved
0.7632	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD8293	Discontinued
0.7623	Intermediate Similarity	NPD7078	Approved
0.7583	Intermediate Similarity	NPD5988	Approved
0.7583	Intermediate Similarity	NPD6370	Approved
0.757	Intermediate Similarity	NPD5222	Approved
0.757	Intermediate Similarity	NPD4697	Phase 3
0.757	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5221	Approved
0.7547	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7900	Approved
0.7545	Intermediate Similarity	NPD4633	Approved
0.7545	Intermediate Similarity	NPD5226	Approved
0.7545	Intermediate Similarity	NPD5224	Approved
0.7545	Intermediate Similarity	NPD5211	Phase 2
0.7545	Intermediate Similarity	NPD5225	Approved
0.7544	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6336	Discontinued
0.7521	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD4767	Approved
0.7477	Intermediate Similarity	NPD5174	Approved
0.7477	Intermediate Similarity	NPD5175	Approved
0.7458	Intermediate Similarity	NPD7115	Discovery
0.7455	Intermediate Similarity	NPD5223	Approved
0.7453	Intermediate Similarity	NPD6399	Phase 3
0.7431	Intermediate Similarity	NPD7638	Approved
0.7411	Intermediate Similarity	NPD5141	Approved
0.7379	Intermediate Similarity	NPD3618	Phase 1
0.7368	Intermediate Similarity	NPD4730	Approved
0.7368	Intermediate Similarity	NPD4729	Approved
0.7364	Intermediate Similarity	NPD7640	Approved
0.7364	Intermediate Similarity	NPD7639	Approved
0.7358	Intermediate Similarity	NPD6411	Approved
0.7358	Intermediate Similarity	NPD6079	Approved
0.7355	Intermediate Similarity	NPD6921	Approved
0.7333	Intermediate Similarity	NPD7100	Approved
0.7333	Intermediate Similarity	NPD7101	Approved
0.7321	Intermediate Similarity	NPD4754	Approved
0.7315	Intermediate Similarity	NPD5695	Phase 3
0.7311	Intermediate Similarity	NPD6317	Approved
0.7281	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4225	Approved
0.7273	Intermediate Similarity	NPD5696	Approved
0.7264	Intermediate Similarity	NPD46	Approved
0.7264	Intermediate Similarity	NPD6698	Approved
0.725	Intermediate Similarity	NPD6335	Approved
0.725	Intermediate Similarity	NPD6313	Approved
0.725	Intermediate Similarity	NPD6314	Approved
0.7241	Intermediate Similarity	NPD5247	Approved
0.7241	Intermediate Similarity	NPD5251	Approved
0.7241	Intermediate Similarity	NPD5249	Phase 3
0.7241	Intermediate Similarity	NPD5250	Approved
0.7241	Intermediate Similarity	NPD5248	Approved
0.7238	Intermediate Similarity	NPD5737	Approved
0.7238	Intermediate Similarity	NPD6672	Approved
0.7227	Intermediate Similarity	NPD6868	Approved
0.7217	Intermediate Similarity	NPD5128	Approved
0.7213	Intermediate Similarity	NPD6908	Approved
0.7213	Intermediate Similarity	NPD6909	Approved
0.719	Intermediate Similarity	NPD7516	Approved
0.717	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4753	Phase 2
0.717	Intermediate Similarity	NPD6101	Approved
0.7157	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD6033	Approved
0.713	Intermediate Similarity	NPD4202	Approved
0.7129	Intermediate Similarity	NPD4695	Discontinued
0.7107	Intermediate Similarity	NPD7328	Approved
0.7107	Intermediate Similarity	NPD7327	Approved
0.7075	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8033	Approved
0.7059	Intermediate Similarity	NPD8133	Approved
0.7048	Intermediate Similarity	NPD5330	Approved
0.7048	Intermediate Similarity	NPD6409	Approved
0.7048	Intermediate Similarity	NPD7146	Approved
0.7048	Intermediate Similarity	NPD6684	Approved
0.7048	Intermediate Similarity	NPD7521	Approved
0.7048	Intermediate Similarity	NPD7334	Approved
0.7034	Intermediate Similarity	NPD5215	Approved
0.7034	Intermediate Similarity	NPD5217	Approved
0.7034	Intermediate Similarity	NPD5216	Approved
0.7019	Intermediate Similarity	NPD3666	Approved
0.7019	Intermediate Similarity	NPD3133	Approved
0.7019	Intermediate Similarity	NPD4786	Approved
0.7019	Intermediate Similarity	NPD3665	Phase 1
0.6992	Remote Similarity	NPD8377	Approved
0.6992	Remote Similarity	NPD8294	Approved
0.6977	Remote Similarity	NPD7260	Phase 2
0.6972	Remote Similarity	NPD5779	Approved
0.6972	Remote Similarity	NPD5778	Approved
0.6949	Remote Similarity	NPD5169	Approved
0.6949	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5135	Approved
0.6935	Remote Similarity	NPD8296	Approved
0.6935	Remote Similarity	NPD8378	Approved
0.6935	Remote Similarity	NPD8517	Approved
0.6935	Remote Similarity	NPD8335	Approved
0.6935	Remote Similarity	NPD8515	Approved
0.6935	Remote Similarity	NPD8380	Approved
0.6935	Remote Similarity	NPD7503	Approved
0.6935	Remote Similarity	NPD8516	Approved
0.6935	Remote Similarity	NPD8379	Approved
0.6935	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD5168	Approved
0.6916	Remote Similarity	NPD6903	Approved
0.6909	Remote Similarity	NPD5282	Discontinued
0.6891	Remote Similarity	NPD5127	Approved
0.6887	Remote Similarity	NPD5279	Phase 3
0.6881	Remote Similarity	NPD8035	Phase 2
0.6881	Remote Similarity	NPD8034	Phase 2
0.6881	Remote Similarity	NPD7983	Approved
0.6852	Remote Similarity	NPD6080	Approved
0.6852	Remote Similarity	NPD6904	Approved
0.6852	Remote Similarity	NPD6673	Approved
0.6847	Remote Similarity	NPD4629	Approved
0.6847	Remote Similarity	NPD5210	Approved
0.6842	Remote Similarity	NPD5344	Discontinued
0.6833	Remote Similarity	NPD6053	Discontinued
0.6825	Remote Similarity	NPD6067	Discontinued
0.6792	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7632	Discontinued
0.675	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5693	Phase 1
0.6721	Remote Similarity	NPD5167	Approved
0.6699	Remote Similarity	NPD7645	Phase 2
0.6698	Remote Similarity	NPD3668	Phase 3
0.6698	Remote Similarity	NPD4197	Approved
0.6696	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6334	Approved
0.6667	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD6333	Approved
0.6636	Remote Similarity	NPD5329	Approved
0.6636	Remote Similarity	NPD5692	Phase 3
0.6602	Remote Similarity	NPD3617	Approved
0.6577	Remote Similarity	NPD5281	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