NPASS Compound

Structure

CID50124 OpenBabel06191715382D 36 39 0 0 1 0 0 0 0 0999 V2000 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0029 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 23 1 0 0 0 0 10 16 1 0 0 0 0 10 17 2 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 27 2 0 0 0 0 12 33 1 0 0 0 0 13 28 2 0 0 0 0 13 34 1 0 0 0 0 14 29 2 0 0 0 0 14 35 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 20 1 0 0 0 0 16 24 1 1 0 0 0 17 36 1 0 0 0 0 18 24 1 6 0 0 0 18 33 1 0 0 0 0 19 30 2 0 0 0 0 19 36 1 0 0 0 0 20 21 1 0 0 0 0 20 25 1 6 0 0 0 21 22 1 0 0 0 0 21 34 1 1 0 0 0 22 26 1 6 0 0 0 22 35 1 0 0 0 0 23 26 1 0 0 0 0 24 26 1 1 0 0 0 25 7 1 6 0 0 0 25 31 1 0 0 0 0 26 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.22
Volume:	496.11
LogP:	2.517
LogD:	1.722
LogS:	-3.931
# Rotatable Bonds:	6
TPSA:	152.73
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	5.28
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.267
MDCK Permeability:	6.359394319588318e-05
Pgp-inhibitor:	0.286
Pgp-substrate:	0.746
Human Intestinal Absorption (HIA):	0.793
20% Bioavailability (F20%):	0.321
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.815
Plasma Protein Binding (PPB):	67.05773162841797%
Volume Distribution (VD):	1.191
Pgp-substrate:	26.286680221557617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.084
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.216
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	2.469
Half-life (T1/2):	0.369

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.92
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.97
Maximum Recommended Daily Dose:	0.525
Skin Sensitization:	0.257
Carcinogencity:	0.912
Eye Corrosion:	0.004
Eye Irritation:	0.01
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC50124

Natural Product ID:	NPC50124
*Common Name:**	Neocaesalpin O
IUPAC Name:	[(1S,4aR,5S,6R,6aS,7S,11aS,11bS)-5,6-diacetyloxy-4a,7-dihydroxy-4,4,7,11b-tetramethyl-9-oxo-2,3,5,6,6a,11a-hexahydro-1H-naphtho[2,1-f][1]benzofuran-1-yl] acetate
Synonyms:
Standard InCHIKey:	XKLBSFHFNUCCKY-UXYMEOMDSA-N
Standard InCHI:	InChI=1S/C26H34O10/c1-12(27)33-18-8-9-23(4,5)26(32)22(35-14(3)29)21(34-13(2)28)20-16(24(18,26)6)10-17-15(25(20,7)31)11-19(30)36-17/h10-11,16,18,20-22,31-32H,8-9H2,1-7H3/t16-,18-,20-,21+,22-,24-,25+,26+/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@@H]2[C@H](C=C3C(=CC(=O)O3)[C@@]2(C)O)[C@@]2([C@]([C@H]1OC(=O)C)(O)C(C)(C)CC[C@@H]2OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386711
PubChem CID:	73351991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678648]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15921414]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	seed kernel	n.a.	PMID[15921414]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[23806110]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24303808]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26402	Caesalpinia crista	Species	Fabaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	41200.0	nM	PMID[475810]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[475810]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[475810]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[475810]

☑ 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 NPC50124 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	219
0.1-0.2	1364
0.2-0.3	3870
0.3-0.4	6001
0.4-0.5	13423
0.5-0.6	10093
0.6-0.7	5909
0.7-0.8	1711
0.8-0.85	83
0.85-0.9	21
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9406	High Similarity	NPC471206
0.92	High Similarity	NPC472554
0.9109	High Similarity	NPC472552
0.9109	High Similarity	NPC11956
0.9048	High Similarity	NPC177047
0.902	High Similarity	NPC23584
0.8942	High Similarity	NPC122816
0.8911	High Similarity	NPC38855
0.8812	High Similarity	NPC278673
0.8762	High Similarity	NPC471205
0.8667	High Similarity	NPC51719
0.8641	High Similarity	NPC11974
0.8571	High Similarity	NPC473543
0.8515	High Similarity	NPC276110
0.8505	High Similarity	NPC181994
0.8505	High Similarity	NPC38948
0.8491	Intermediate Similarity	NPC81630
0.8476	Intermediate Similarity	NPC45897
0.8476	Intermediate Similarity	NPC281378
0.8476	Intermediate Similarity	NPC474822
0.8476	Intermediate Similarity	NPC473523
0.8476	Intermediate Similarity	NPC474124
0.8462	Intermediate Similarity	NPC475617
0.8426	Intermediate Similarity	NPC206618
0.8411	Intermediate Similarity	NPC475074
0.8411	Intermediate Similarity	NPC187435
0.8411	Intermediate Similarity	NPC67321
0.8411	Intermediate Similarity	NPC473586
0.8381	Intermediate Similarity	NPC475344
0.8381	Intermediate Similarity	NPC476471
0.8365	Intermediate Similarity	NPC188968
0.8364	Intermediate Similarity	NPC470025
0.8364	Intermediate Similarity	NPC328074
0.8364	Intermediate Similarity	NPC321272
0.8364	Intermediate Similarity	NPC317460
0.835	Intermediate Similarity	NPC199099
0.835	Intermediate Similarity	NPC473244
0.8333	Intermediate Similarity	NPC475263
0.8318	Intermediate Similarity	NPC34768
0.8317	Intermediate Similarity	NPC110022
0.8317	Intermediate Similarity	NPC53555
0.8317	Intermediate Similarity	NPC7349
0.8302	Intermediate Similarity	NPC474575
0.8288	Intermediate Similarity	NPC471204
0.8288	Intermediate Similarity	NPC470027
0.8273	Intermediate Similarity	NPC132790
0.8273	Intermediate Similarity	NPC17791
0.8273	Intermediate Similarity	NPC247031
0.8273	Intermediate Similarity	NPC100329
0.8273	Intermediate Similarity	NPC97939
0.8269	Intermediate Similarity	NPC325229
0.8269	Intermediate Similarity	NPC275086
0.8261	Intermediate Similarity	NPC233500
0.8257	Intermediate Similarity	NPC475586
0.8252	Intermediate Similarity	NPC221801
0.8252	Intermediate Similarity	NPC260796
0.8252	Intermediate Similarity	NPC129569
0.8252	Intermediate Similarity	NPC284194
0.8252	Intermediate Similarity	NPC211810
0.8252	Intermediate Similarity	NPC471765
0.8241	Intermediate Similarity	NPC302788
0.8235	Intermediate Similarity	NPC105490
0.8224	Intermediate Similarity	NPC200861
0.8208	Intermediate Similarity	NPC109195
0.8208	Intermediate Similarity	NPC475038
0.8198	Intermediate Similarity	NPC269530
0.819	Intermediate Similarity	NPC230546
0.819	Intermediate Similarity	NPC196130
0.819	Intermediate Similarity	NPC473510
0.819	Intermediate Similarity	NPC271295
0.819	Intermediate Similarity	NPC79303
0.8182	Intermediate Similarity	NPC478211
0.8182	Intermediate Similarity	NPC316708
0.8174	Intermediate Similarity	NPC112936
0.8173	Intermediate Similarity	NPC51499
0.8173	Intermediate Similarity	NPC120446
0.8173	Intermediate Similarity	NPC210337
0.8165	Intermediate Similarity	NPC88701
0.8165	Intermediate Similarity	NPC306265
0.8158	Intermediate Similarity	NPC478206
0.8158	Intermediate Similarity	NPC108581
0.8158	Intermediate Similarity	NPC478205
0.8148	Intermediate Similarity	NPC88349
0.8136	Intermediate Similarity	NPC477745
0.8131	Intermediate Similarity	NPC120009
0.8125	Intermediate Similarity	NPC475966
0.8125	Intermediate Similarity	NPC478212
0.8119	Intermediate Similarity	NPC78973
0.8113	Intermediate Similarity	NPC235920
0.8113	Intermediate Similarity	NPC96784
0.8108	Intermediate Similarity	NPC470026
0.8091	Intermediate Similarity	NPC316974
0.8091	Intermediate Similarity	NPC478210
0.8091	Intermediate Similarity	NPC299590
0.8087	Intermediate Similarity	NPC213761
0.8087	Intermediate Similarity	NPC219656
0.8087	Intermediate Similarity	NPC278681
0.8087	Intermediate Similarity	NPC35171
0.8077	Intermediate Similarity	NPC165632
0.8077	Intermediate Similarity	NPC88009
0.8077	Intermediate Similarity	NPC473153
0.8077	Intermediate Similarity	NPC16967
0.8077	Intermediate Similarity	NPC194132
0.8077	Intermediate Similarity	NPC472995
0.8073	Intermediate Similarity	NPC179380
0.8073	Intermediate Similarity	NPC475781
0.807	Intermediate Similarity	NPC478204
0.807	Intermediate Similarity	NPC473968
0.807	Intermediate Similarity	NPC203862
0.8067	Intermediate Similarity	NPC476008
0.8058	Intermediate Similarity	NPC182826
0.8058	Intermediate Similarity	NPC472360
0.8058	Intermediate Similarity	NPC140277
0.8058	Intermediate Similarity	NPC472416
0.8058	Intermediate Similarity	NPC469491
0.8058	Intermediate Similarity	NPC105375
0.8056	Intermediate Similarity	NPC472822
0.8037	Intermediate Similarity	NPC472815
0.8037	Intermediate Similarity	NPC295791
0.8037	Intermediate Similarity	NPC476081
0.8036	Intermediate Similarity	NPC472002
0.8036	Intermediate Similarity	NPC42658
0.8036	Intermediate Similarity	NPC44537
0.802	Intermediate Similarity	NPC16265
0.802	Intermediate Similarity	NPC170633
0.802	Intermediate Similarity	NPC246028
0.8019	Intermediate Similarity	NPC474190
0.8019	Intermediate Similarity	NPC324841
0.8019	Intermediate Similarity	NPC474571
0.8019	Intermediate Similarity	NPC272223
0.8019	Intermediate Similarity	NPC16601
0.8019	Intermediate Similarity	NPC254567
0.8	Intermediate Similarity	NPC218093
0.8	Intermediate Similarity	NPC254121
0.8	Intermediate Similarity	NPC16701
0.8	Intermediate Similarity	NPC311223
0.8	Intermediate Similarity	NPC205143
0.8	Intermediate Similarity	NPC48548
0.8	Intermediate Similarity	NPC470024
0.8	Intermediate Similarity	NPC217921
0.8	Intermediate Similarity	NPC135015
0.8	Intermediate Similarity	NPC128795
0.7982	Intermediate Similarity	NPC82251
0.7982	Intermediate Similarity	NPC111952
0.7982	Intermediate Similarity	NPC478216
0.7982	Intermediate Similarity	NPC119855
0.7982	Intermediate Similarity	NPC470075
0.7982	Intermediate Similarity	NPC186668
0.7982	Intermediate Similarity	NPC220217
0.7966	Intermediate Similarity	NPC67251
0.7965	Intermediate Similarity	NPC171126
0.7963	Intermediate Similarity	NPC196471
0.7963	Intermediate Similarity	NPC10232
0.7963	Intermediate Similarity	NPC189588
0.7963	Intermediate Similarity	NPC187302
0.7963	Intermediate Similarity	NPC472821
0.7963	Intermediate Similarity	NPC97487
0.7963	Intermediate Similarity	NPC159533
0.7961	Intermediate Similarity	NPC472641
0.7961	Intermediate Similarity	NPC472640
0.7946	Intermediate Similarity	NPC469655
0.7946	Intermediate Similarity	NPC470076
0.7946	Intermediate Similarity	NPC469656
0.7946	Intermediate Similarity	NPC474846
0.7941	Intermediate Similarity	NPC221111
0.7941	Intermediate Similarity	NPC280149
0.7931	Intermediate Similarity	NPC291820
0.7931	Intermediate Similarity	NPC81222
0.7931	Intermediate Similarity	NPC153085
0.7931	Intermediate Similarity	NPC268326
0.7928	Intermediate Similarity	NPC40728
0.7928	Intermediate Similarity	NPC472216
0.7928	Intermediate Similarity	NPC5475
0.7928	Intermediate Similarity	NPC284828
0.7928	Intermediate Similarity	NPC173905
0.7925	Intermediate Similarity	NPC247233
0.7925	Intermediate Similarity	NPC477876
0.7925	Intermediate Similarity	NPC477875
0.7925	Intermediate Similarity	NPC475068
0.7921	Intermediate Similarity	NPC106332
0.7913	Intermediate Similarity	NPC142066
0.7913	Intermediate Similarity	NPC474418
0.7913	Intermediate Similarity	NPC243196
0.7913	Intermediate Similarity	NPC53396
0.7913	Intermediate Similarity	NPC77319
0.7913	Intermediate Similarity	NPC27507
0.7913	Intermediate Similarity	NPC309034
0.7913	Intermediate Similarity	NPC473590
0.7913	Intermediate Similarity	NPC84987
0.7913	Intermediate Similarity	NPC244402
0.7913	Intermediate Similarity	NPC157376
0.7913	Intermediate Similarity	NPC99728
0.7913	Intermediate Similarity	NPC50305
0.7913	Intermediate Similarity	NPC157380
0.7913	Intermediate Similarity	NPC87250
0.7913	Intermediate Similarity	NPC471353
0.7913	Intermediate Similarity	NPC98249
0.7913	Intermediate Similarity	NPC34390
0.7913	Intermediate Similarity	NPC158344
0.7913	Intermediate Similarity	NPC185287

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 NPC50124 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1475
0.2-0.3	3527
0.3-0.4	2456
0.4-0.5	1022
0.5-0.6	316
0.6-0.7	146
0.7-0.8	24
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8091	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7503	Approved
0.7931	Intermediate Similarity	NPD7516	Approved
0.785	Intermediate Similarity	NPD6648	Approved
0.7845	Intermediate Similarity	NPD7328	Approved
0.7845	Intermediate Similarity	NPD7327	Approved
0.7778	Intermediate Similarity	NPD5344	Discontinued
0.7748	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD7640	Approved
0.7685	Intermediate Similarity	NPD7639	Approved
0.7647	Intermediate Similarity	NPD8335	Approved
0.7647	Intermediate Similarity	NPD8296	Approved
0.7647	Intermediate Similarity	NPD8380	Approved
0.7647	Intermediate Similarity	NPD8378	Approved
0.7647	Intermediate Similarity	NPD8379	Approved
0.7647	Intermediate Similarity	NPD8033	Approved
0.7593	Intermediate Similarity	NPD4225	Approved
0.7593	Intermediate Similarity	NPD7638	Approved
0.7563	Intermediate Similarity	NPD8294	Approved
0.7563	Intermediate Similarity	NPD8377	Approved
0.7522	Intermediate Similarity	NPD6686	Approved
0.7311	Intermediate Similarity	NPD7115	Discovery
0.7308	Intermediate Similarity	NPD7524	Approved
0.7258	Intermediate Similarity	NPD7507	Approved
0.7232	Intermediate Similarity	NPD7632	Discontinued
0.7222	Intermediate Similarity	NPD7319	Approved
0.7103	Intermediate Similarity	NPD7838	Discovery
0.7069	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6695	Phase 3
0.6881	Remote Similarity	NPD7637	Suspended
0.6864	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6319	Approved
0.6842	Remote Similarity	NPD4159	Approved
0.6833	Remote Similarity	NPD6053	Discontinued
0.6833	Remote Similarity	NPD8297	Approved
0.6814	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8515	Approved
0.68	Remote Similarity	NPD8517	Approved
0.68	Remote Similarity	NPD8516	Approved
0.68	Remote Similarity	NPD8513	Phase 3
0.6789	Remote Similarity	NPD6698	Approved
0.6789	Remote Similarity	NPD46	Approved
0.6777	Remote Similarity	NPD4632	Approved
0.6757	Remote Similarity	NPD7748	Approved
0.6752	Remote Similarity	NPD6675	Approved
0.6752	Remote Similarity	NPD7128	Approved
0.6752	Remote Similarity	NPD6402	Approved
0.6752	Remote Similarity	NPD5739	Approved
0.6726	Remote Similarity	NPD7902	Approved
0.6723	Remote Similarity	NPD6373	Approved
0.6723	Remote Similarity	NPD6372	Approved
0.6698	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6051	Approved
0.6695	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6399	Phase 3
0.6639	Remote Similarity	NPD8133	Approved
0.6639	Remote Similarity	NPD6899	Approved
0.6639	Remote Similarity	NPD7320	Approved
0.6639	Remote Similarity	NPD6881	Approved
0.6635	Remote Similarity	NPD6930	Phase 2
0.6635	Remote Similarity	NPD6931	Approved
0.6612	Remote Similarity	NPD6649	Approved
0.6612	Remote Similarity	NPD6650	Approved
0.661	Remote Similarity	NPD6008	Approved
0.6591	Remote Similarity	NPD7260	Phase 2
0.6577	Remote Similarity	NPD7515	Phase 2
0.6562	Remote Similarity	NPD8328	Phase 3
0.6557	Remote Similarity	NPD6882	Approved
0.6555	Remote Similarity	NPD5697	Approved
0.6555	Remote Similarity	NPD5701	Approved
0.6538	Remote Similarity	NPD6929	Approved
0.6538	Remote Similarity	NPD8074	Phase 3
0.6535	Remote Similarity	NPD6921	Approved
0.6529	Remote Similarity	NPD6883	Approved
0.6529	Remote Similarity	NPD7102	Approved
0.6529	Remote Similarity	NPD6371	Approved
0.6529	Remote Similarity	NPD7290	Approved
0.6518	Remote Similarity	NPD5779	Approved
0.6518	Remote Similarity	NPD5778	Approved
0.6512	Remote Similarity	NPD7492	Approved
0.6509	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6009	Approved
0.648	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7514	Phase 3
0.6476	Remote Similarity	NPD7525	Registered
0.6476	Remote Similarity	NPD7332	Phase 2
0.6475	Remote Similarity	NPD6847	Approved
0.6475	Remote Similarity	NPD6869	Approved
0.6475	Remote Similarity	NPD6617	Approved
0.6475	Remote Similarity	NPD8130	Phase 1
0.6462	Remote Similarity	NPD6616	Approved
0.646	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7900	Approved
0.6457	Remote Similarity	NPD6059	Approved
0.6457	Remote Similarity	NPD6054	Approved
0.6446	Remote Similarity	NPD6012	Approved
0.6446	Remote Similarity	NPD6013	Approved
0.6446	Remote Similarity	NPD6014	Approved
0.6435	Remote Similarity	NPD6084	Phase 2
0.6435	Remote Similarity	NPD6083	Phase 2
0.6434	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD7087	Discontinued
0.6429	Remote Similarity	NPD7983	Approved
0.6418	Remote Similarity	NPD6845	Suspended
0.6417	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD7078	Approved
0.6412	Remote Similarity	NPD8293	Discontinued
0.6406	Remote Similarity	NPD5983	Phase 2
0.6396	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7645	Phase 2
0.6364	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7736	Approved
0.6364	Remote Similarity	NPD6011	Approved
0.6364	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD6370	Approved
0.6356	Remote Similarity	NPD5211	Phase 2
0.6346	Remote Similarity	NPD6925	Approved
0.6346	Remote Similarity	NPD5776	Phase 2
0.6341	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6336	Discontinued
0.6333	Remote Similarity	NPD6640	Phase 3
0.633	Remote Similarity	NPD6893	Approved
0.633	Remote Similarity	NPD1694	Approved
0.6294	Remote Similarity	NPD7625	Phase 1
0.6293	Remote Similarity	NPD4755	Approved
0.6286	Remote Similarity	NPD7145	Approved
0.6283	Remote Similarity	NPD6411	Approved
0.6279	Remote Similarity	NPD6016	Approved
0.6279	Remote Similarity	NPD6015	Approved
0.6273	Remote Similarity	NPD7146	Approved
0.6273	Remote Similarity	NPD6409	Approved
0.6273	Remote Similarity	NPD7521	Approved
0.6273	Remote Similarity	NPD3618	Phase 1
0.6273	Remote Similarity	NPD5330	Approved
0.6273	Remote Similarity	NPD6684	Approved
0.6273	Remote Similarity	NPD7334	Approved
0.6262	Remote Similarity	NPD6902	Approved
0.6262	Remote Similarity	NPD6898	Phase 1
0.6261	Remote Similarity	NPD5695	Phase 3
0.626	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD6933	Approved
0.6239	Remote Similarity	NPD5696	Approved
0.6231	Remote Similarity	NPD5988	Approved
0.6228	Remote Similarity	NPD4202	Approved
0.6195	Remote Similarity	NPD3168	Discontinued
0.619	Remote Similarity	NPD6932	Approved
0.6186	Remote Similarity	NPD4700	Approved
0.6186	Remote Similarity	NPD5286	Approved
0.6186	Remote Similarity	NPD5285	Approved
0.6186	Remote Similarity	NPD4696	Approved
0.6161	Remote Similarity	NPD6672	Approved
0.6161	Remote Similarity	NPD5737	Approved
0.6161	Remote Similarity	NPD6903	Approved
0.6161	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8264	Approved
0.6154	Remote Similarity	NPD7339	Approved
0.6154	Remote Similarity	NPD6942	Approved
0.6142	Remote Similarity	NPD6274	Approved
0.614	Remote Similarity	NPD5693	Phase 1
0.614	Remote Similarity	NPD5284	Approved
0.614	Remote Similarity	NPD8034	Phase 2
0.614	Remote Similarity	NPD6079	Approved
0.614	Remote Similarity	NPD5281	Approved
0.614	Remote Similarity	NPD8035	Phase 2
0.6124	Remote Similarity	NPD7100	Approved
0.6124	Remote Similarity	NPD7101	Approved
0.6121	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD6101	Approved
0.6095	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4786	Approved
0.6083	Remote Similarity	NPD5225	Approved
0.6083	Remote Similarity	NPD4633	Approved
0.6083	Remote Similarity	NPD5224	Approved
0.6083	Remote Similarity	NPD5226	Approved
0.6075	Remote Similarity	NPD6683	Phase 2
0.6071	Remote Similarity	NPD3573	Approved
0.6071	Remote Similarity	NPD4250	Approved
0.6071	Remote Similarity	NPD4251	Approved
0.6066	Remote Similarity	NPD4767	Approved
0.6066	Remote Similarity	NPD4768	Approved
0.6061	Remote Similarity	NPD6067	Discontinued
0.6058	Remote Similarity	NPD6926	Approved
0.6058	Remote Similarity	NPD6924	Approved
0.6055	Remote Similarity	NPD3667	Approved
0.6047	Remote Similarity	NPD6335	Approved
0.6036	Remote Similarity	NPD1696	Phase 3
0.6034	Remote Similarity	NPD5282	Discontinued
0.6033	Remote Similarity	NPD5174	Approved
0.6033	Remote Similarity	NPD5175	Approved
0.6031	Remote Similarity	NPD6909	Approved
0.6031	Remote Similarity	NPD6908	Approved
0.6019	Remote Similarity	NPD7509	Discontinued
0.6	Remote Similarity	NPD6033	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