NPASS Compound

Structure

NPC471205 OpenBabel07101718182D 33 36 0 0 1 0 0 0 0 0999 V2000 -1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7812 0.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 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 -5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4152 -1.6910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -1.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 -4.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 -0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.6910 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 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 21 1 0 0 0 0 5 21 1 0 0 0 0 6 22 1 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 15 1 0 0 0 0 8 23 1 0 0 0 0 9 16 1 0 0 0 0 9 24 1 0 0 0 0 10 17 1 0 0 0 0 10 21 1 0 0 0 0 11 1 1 1 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 25 2 0 0 0 0 12 31 1 0 0 0 0 13 26 2 0 0 0 0 13 32 1 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 22 1 6 0 0 0 16 19 1 0 0 0 0 16 27 1 6 0 0 0 17 20 1 0 0 0 0 17 31 1 0 0 0 0 18 28 2 0 0 0 0 18 33 1 0 0 0 0 20 22 1 0 0 0 0 20 32 1 0 0 0 0 21 24 1 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 23 33 1 0 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.22
Volume:	458.0
LogP:	2.061
LogD:	1.885
LogS:	-3.535
# Rotatable Bonds:	4
TPSA:	139.59
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	5.357
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.324
MDCK Permeability:	7.77653549448587e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.811
Human Intestinal Absorption (HIA):	0.952
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.892
Plasma Protein Binding (PPB):	33.92423629760742%
Volume Distribution (VD):	0.783
Pgp-substrate:	40.58378219604492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.425
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.207
CYP3A4-substrate:	0.67

ADMET: Excretion

Clearance (CL):	3.045
Half-life (T1/2):	0.671

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.355
Drug-inuced Liver Injury (DILI):	0.287
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.204
Carcinogencity:	0.703
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC471205

Natural Product ID:	NPC471205
*Common Name:**	Neocaesalpin C
IUPAC Name:	[(1R,4aR,6S,6aS,7R,10aR,11aS,11bS)-1-acetyloxy-4a,6,10a-trihydroxy-4,4,7,11b-tetramethyl-9-oxo-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-2-yl] acetate
Synonyms:
Standard InCHIKey:	GCGCZEGAELXNPM-KYKBPDANSA-N
Standard InCHI:	InChI=1S/C24H34O9/c1-11-14-7-18(28)33-23(14,29)8-15-19(11)16(27)9-24(30)21(4,5)10-17(31-12(2)25)20(22(15,24)6)32-13(3)26/h7,11,15-17,19-20,27,29-30H,8-10H2,1-6H3/t11-,15-,16-,17?,19-,20-,22-,23+,24+/m0/s1
SMILES:	CC(=O)O[C@H]1C(OC(=O)C)CC([C@]2([C@@]1(C)[C@H]1C[C@@]3(O)OC(=O)C=C3[C@@H]([C@@H]1[C@H](C2)O)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386710
PubChem CID:	73350468
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]
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]
NPO14392	Caesalpinia minax	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	=	36100.0	nM	PMID[515745]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[515745]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	31900.0	nM	PMID[515745]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[515745]

☑ 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 NPC471205 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	216
0.1-0.2	1540
0.2-0.3	4412
0.3-0.4	7479
0.4-0.5	13298
0.5-0.6	7452
0.6-0.7	5490
0.7-0.8	2515
0.8-0.85	252
0.85-0.9	34
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC51719
0.96	High Similarity	NPC122816
0.932	High Similarity	NPC177047
0.93	High Similarity	NPC281378
0.91	High Similarity	NPC11974
0.9	High Similarity	NPC324841
0.9	High Similarity	NPC38855
0.8942	High Similarity	NPC38948
0.8942	High Similarity	NPC181994
0.8932	High Similarity	NPC471206
0.8922	High Similarity	NPC45897
0.8911	High Similarity	NPC472554
0.89	High Similarity	NPC325229
0.89	High Similarity	NPC275086
0.8878	High Similarity	NPC105490
0.8857	High Similarity	NPC206618
0.8824	High Similarity	NPC472552
0.8824	High Similarity	NPC475038
0.8824	High Similarity	NPC109195
0.8812	High Similarity	NPC16601
0.88	High Similarity	NPC51499
0.8788	High Similarity	NPC276110
0.8776	High Similarity	NPC7349
0.8762	High Similarity	NPC50124
0.8738	High Similarity	NPC473523
0.8738	High Similarity	NPC474822
0.8727	High Similarity	NPC83287
0.8673	High Similarity	NPC329842
0.8654	High Similarity	NPC473543
0.8641	High Similarity	NPC472815
0.8636	High Similarity	NPC471351
0.8636	High Similarity	NPC152615
0.8636	High Similarity	NPC157376
0.8636	High Similarity	NPC99728
0.8636	High Similarity	NPC50305
0.8636	High Similarity	NPC471353
0.8636	High Similarity	NPC471355
0.8636	High Similarity	NPC473852
0.8636	High Similarity	NPC243196
0.8636	High Similarity	NPC87250
0.8636	High Similarity	NPC27507
0.8636	High Similarity	NPC84987
0.8636	High Similarity	NPC471354
0.8636	High Similarity	NPC309034
0.8636	High Similarity	NPC244402
0.8636	High Similarity	NPC34390
0.8636	High Similarity	NPC196429
0.8636	High Similarity	NPC77319
0.8636	High Similarity	NPC142066
0.8636	High Similarity	NPC474418
0.8636	High Similarity	NPC158344
0.8586	High Similarity	NPC472641
0.8586	High Similarity	NPC472640
0.8585	High Similarity	NPC88701
0.8571	High Similarity	NPC475136
0.8571	High Similarity	NPC474466
0.8558	High Similarity	NPC97487
0.8558	High Similarity	NPC10232
0.8558	High Similarity	NPC120009
0.8558	High Similarity	NPC196471
0.8558	High Similarity	NPC189588
0.8558	High Similarity	NPC187302
0.8558	High Similarity	NPC471938
0.8558	High Similarity	NPC474575
0.8558	High Similarity	NPC160583
0.8545	High Similarity	NPC5311
0.8545	High Similarity	NPC193382
0.8545	High Similarity	NPC99620
0.8545	High Similarity	NPC199428
0.8545	High Similarity	NPC471816
0.8545	High Similarity	NPC310341
0.8544	High Similarity	NPC477717
0.8529	High Similarity	NPC278673
0.8515	High Similarity	NPC165632
0.8515	High Similarity	NPC194132
0.8505	High Similarity	NPC475030
0.8505	High Similarity	NPC475586
0.85	High Similarity	NPC140277
0.8491	Intermediate Similarity	NPC475074
0.8491	Intermediate Similarity	NPC187435
0.8491	Intermediate Similarity	NPC472820
0.8491	Intermediate Similarity	NPC67321
0.8491	Intermediate Similarity	NPC473586
0.8485	Intermediate Similarity	NPC78594
0.8482	Intermediate Similarity	NPC329905
0.8476	Intermediate Similarity	NPC471937
0.8468	Intermediate Similarity	NPC93883
0.8462	Intermediate Similarity	NPC11956
0.8462	Intermediate Similarity	NPC476471
0.8462	Intermediate Similarity	NPC471914
0.8462	Intermediate Similarity	NPC121423
0.8462	Intermediate Similarity	NPC475344
0.8455	Intermediate Similarity	NPC471633
0.8455	Intermediate Similarity	NPC31354
0.8455	Intermediate Similarity	NPC84949
0.8455	Intermediate Similarity	NPC69576
0.8447	Intermediate Similarity	NPC477716
0.8447	Intermediate Similarity	NPC477721
0.8431	Intermediate Similarity	NPC477719
0.8431	Intermediate Similarity	NPC473244
0.8431	Intermediate Similarity	NPC477718
0.8421	Intermediate Similarity	NPC264336
0.8416	Intermediate Similarity	NPC471915
0.8411	Intermediate Similarity	NPC475263
0.8407	Intermediate Similarity	NPC475629
0.8407	Intermediate Similarity	NPC475556
0.84	Intermediate Similarity	NPC110022
0.84	Intermediate Similarity	NPC53555
0.8396	Intermediate Similarity	NPC220217
0.8396	Intermediate Similarity	NPC186668
0.8396	Intermediate Similarity	NPC472818
0.8396	Intermediate Similarity	NPC119855
0.8384	Intermediate Similarity	NPC78973
0.8384	Intermediate Similarity	NPC472642
0.8381	Intermediate Similarity	NPC165608
0.8381	Intermediate Similarity	NPC23584
0.8381	Intermediate Similarity	NPC472821
0.8381	Intermediate Similarity	NPC474124
0.8365	Intermediate Similarity	NPC247701
0.8365	Intermediate Similarity	NPC235920
0.8365	Intermediate Similarity	NPC25177
0.8365	Intermediate Similarity	NPC96784
0.8365	Intermediate Similarity	NPC475617
0.8365	Intermediate Similarity	NPC222875
0.8365	Intermediate Similarity	NPC268829
0.8365	Intermediate Similarity	NPC295110
0.8349	Intermediate Similarity	NPC17791
0.8333	Intermediate Similarity	NPC472995
0.8333	Intermediate Similarity	NPC475380
0.8333	Intermediate Similarity	NPC284194
0.8333	Intermediate Similarity	NPC471765
0.8333	Intermediate Similarity	NPC40749
0.8333	Intermediate Similarity	NPC322912
0.8333	Intermediate Similarity	NPC209297
0.8333	Intermediate Similarity	NPC211810
0.8333	Intermediate Similarity	NPC314535
0.8333	Intermediate Similarity	NPC173555
0.8333	Intermediate Similarity	NPC221801
0.8319	Intermediate Similarity	NPC29639
0.8319	Intermediate Similarity	NPC304260
0.8319	Intermediate Similarity	NPC32177
0.8319	Intermediate Similarity	NPC236973
0.8319	Intermediate Similarity	NPC55532
0.8319	Intermediate Similarity	NPC44899
0.8319	Intermediate Similarity	NPC30483
0.8319	Intermediate Similarity	NPC470897
0.8319	Intermediate Similarity	NPC5883
0.8319	Intermediate Similarity	NPC292467
0.8319	Intermediate Similarity	NPC469756
0.8304	Intermediate Similarity	NPC290693
0.8304	Intermediate Similarity	NPC473968
0.8304	Intermediate Similarity	NPC203862
0.8302	Intermediate Similarity	NPC472819
0.8286	Intermediate Similarity	NPC476081
0.8273	Intermediate Similarity	NPC473125
0.8273	Intermediate Similarity	NPC470025
0.8273	Intermediate Similarity	NPC321272
0.8273	Intermediate Similarity	NPC317460
0.8273	Intermediate Similarity	NPC328074
0.8269	Intermediate Similarity	NPC476767
0.8269	Intermediate Similarity	NPC161527
0.8269	Intermediate Similarity	NPC477972
0.8269	Intermediate Similarity	NPC272223
0.8269	Intermediate Similarity	NPC477971
0.8269	Intermediate Similarity	NPC477968
0.8269	Intermediate Similarity	NPC219285
0.8269	Intermediate Similarity	NPC230546
0.8269	Intermediate Similarity	NPC20113
0.8269	Intermediate Similarity	NPC228251
0.8269	Intermediate Similarity	NPC251680
0.8269	Intermediate Similarity	NPC188968
0.8252	Intermediate Similarity	NPC100912
0.8252	Intermediate Similarity	NPC199099
0.8252	Intermediate Similarity	NPC210337
0.8252	Intermediate Similarity	NPC274793
0.8252	Intermediate Similarity	NPC475446
0.8252	Intermediate Similarity	NPC311241
0.8246	Intermediate Similarity	NPC72260
0.8241	Intermediate Similarity	NPC306265
0.8235	Intermediate Similarity	NPC472441
0.8235	Intermediate Similarity	NPC241047
0.8224	Intermediate Similarity	NPC477090
0.8224	Intermediate Similarity	NPC88349
0.8224	Intermediate Similarity	NPC218158
0.8224	Intermediate Similarity	NPC239961
0.8218	Intermediate Similarity	NPC472812
0.8198	Intermediate Similarity	NPC44298
0.8198	Intermediate Similarity	NPC290608
0.8198	Intermediate Similarity	NPC473128
0.8198	Intermediate Similarity	NPC40133
0.8198	Intermediate Similarity	NPC49413
0.8198	Intermediate Similarity	NPC470027
0.8198	Intermediate Similarity	NPC264153
0.8198	Intermediate Similarity	NPC473159
0.819	Intermediate Similarity	NPC49532
0.819	Intermediate Similarity	NPC117445
0.819	Intermediate Similarity	NPC208193
0.819	Intermediate Similarity	NPC473160
0.819	Intermediate Similarity	NPC198992
0.819	Intermediate Similarity	NPC308262

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 NPC471205 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	1690
0.2-0.3	3827
0.3-0.4	2241
0.4-0.5	750
0.5-0.6	273
0.6-0.7	156
0.7-0.8	18
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8818	High Similarity	NPD7516	Approved
0.8727	High Similarity	NPD7327	Approved
0.8727	High Similarity	NPD7328	Approved
0.8333	Intermediate Similarity	NPD8335	Approved
0.8333	Intermediate Similarity	NPD8378	Approved
0.8333	Intermediate Similarity	NPD8380	Approved
0.8333	Intermediate Similarity	NPD8296	Approved
0.8333	Intermediate Similarity	NPD8379	Approved
0.8269	Intermediate Similarity	NPD7640	Approved
0.8269	Intermediate Similarity	NPD7639	Approved
0.8246	Intermediate Similarity	NPD8377	Approved
0.8246	Intermediate Similarity	NPD8294	Approved
0.8174	Intermediate Similarity	NPD8033	Approved
0.8173	Intermediate Similarity	NPD7638	Approved
0.8165	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD6686	Approved
0.8019	Intermediate Similarity	NPD5344	Discontinued
0.7899	Intermediate Similarity	NPD7507	Approved
0.7851	Intermediate Similarity	NPD7319	Approved
0.7818	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD6648	Approved
0.7712	Intermediate Similarity	NPD7503	Approved
0.7664	Intermediate Similarity	NPD4225	Approved
0.7615	Intermediate Similarity	NPD7632	Discontinued
0.7281	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8133	Approved
0.7227	Intermediate Similarity	NPD7115	Discovery
0.7087	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7524	Approved
0.7043	Intermediate Similarity	NPD6412	Phase 2
0.7034	Intermediate Similarity	NPD6882	Approved
0.7034	Intermediate Similarity	NPD8297	Approved
0.703	Intermediate Similarity	NPD7525	Registered
0.7027	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8328	Phase 3
0.6972	Remote Similarity	NPD7748	Approved
0.696	Remote Similarity	NPD7492	Approved
0.6957	Remote Similarity	NPD7128	Approved
0.6957	Remote Similarity	NPD6675	Approved
0.6957	Remote Similarity	NPD6402	Approved
0.6957	Remote Similarity	NPD5739	Approved
0.6944	Remote Similarity	NPD7515	Phase 2
0.6942	Remote Similarity	NPD6009	Approved
0.6937	Remote Similarity	NPD7902	Approved
0.6929	Remote Similarity	NPD7736	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6923	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6373	Approved
0.6911	Remote Similarity	NPD6059	Approved
0.6911	Remote Similarity	NPD6319	Approved
0.6911	Remote Similarity	NPD6054	Approved
0.6905	Remote Similarity	NPD6616	Approved
0.6852	Remote Similarity	NPD6698	Approved
0.6852	Remote Similarity	NPD7838	Discovery
0.6852	Remote Similarity	NPD46	Approved
0.685	Remote Similarity	NPD7078	Approved
0.685	Remote Similarity	NPD8293	Discontinued
0.6838	Remote Similarity	NPD6881	Approved
0.6838	Remote Similarity	NPD6899	Approved
0.6838	Remote Similarity	NPD7320	Approved
0.6833	Remote Similarity	NPD4632	Approved
0.6827	Remote Similarity	NPD6695	Phase 3
0.6812	Remote Similarity	NPD7625	Phase 1
0.6807	Remote Similarity	NPD6649	Approved
0.6807	Remote Similarity	NPD6650	Approved
0.68	Remote Similarity	NPD6370	Approved
0.6789	Remote Similarity	NPD7637	Suspended
0.6765	Remote Similarity	NPD7645	Phase 2
0.6759	Remote Similarity	NPD6051	Approved
0.6752	Remote Similarity	NPD5701	Approved
0.6752	Remote Similarity	NPD5697	Approved
0.6731	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7102	Approved
0.6723	Remote Similarity	NPD7290	Approved
0.6723	Remote Similarity	NPD6883	Approved
0.672	Remote Similarity	NPD8516	Approved
0.672	Remote Similarity	NPD6015	Approved
0.672	Remote Similarity	NPD8513	Phase 3
0.672	Remote Similarity	NPD8515	Approved
0.672	Remote Similarity	NPD6016	Approved
0.672	Remote Similarity	NPD8517	Approved
0.672	Remote Similarity	NPD6921	Approved
0.6697	Remote Similarity	NPD3168	Discontinued
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6013	Approved
0.6639	Remote Similarity	NPD6014	Approved
0.6639	Remote Similarity	NPD6012	Approved
0.6637	Remote Similarity	NPD6083	Phase 2
0.6637	Remote Similarity	NPD6084	Phase 2
0.6614	Remote Similarity	NPD7604	Phase 2
0.6612	Remote Similarity	NPD6053	Discontinued
0.6587	Remote Similarity	NPD5983	Phase 2
0.6583	Remote Similarity	NPD6371	Approved
0.6577	Remote Similarity	NPD6399	Phase 3
0.6574	Remote Similarity	NPD7750	Discontinued
0.6555	Remote Similarity	NPD6011	Approved
0.6552	Remote Similarity	NPD5211	Phase 2
0.6538	Remote Similarity	NPD6930	Phase 2
0.6538	Remote Similarity	NPD6931	Approved
0.6529	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6008	Approved
0.6512	Remote Similarity	NPD6336	Discontinued
0.6491	Remote Similarity	NPD4755	Approved
0.6486	Remote Similarity	NPD8034	Phase 2
0.6486	Remote Similarity	NPD8035	Phase 2
0.6484	Remote Similarity	NPD6067	Discontinued
0.6481	Remote Similarity	NPD3618	Phase 1
0.6466	Remote Similarity	NPD4159	Approved
0.6462	Remote Similarity	NPD8074	Phase 3
0.6455	Remote Similarity	NPD5328	Approved
0.6442	Remote Similarity	NPD6929	Approved
0.6441	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD4202	Approved
0.6422	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6033	Approved
0.6389	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7514	Phase 3
0.6381	Remote Similarity	NPD7332	Phase 2
0.6379	Remote Similarity	NPD5285	Approved
0.6379	Remote Similarity	NPD5286	Approved
0.6379	Remote Similarity	NPD4700	Approved
0.6379	Remote Similarity	NPD4696	Approved
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7087	Discontinued
0.6339	Remote Similarity	NPD6079	Approved
0.6333	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7521	Approved
0.633	Remote Similarity	NPD7146	Approved
0.633	Remote Similarity	NPD6684	Approved
0.633	Remote Similarity	NPD7334	Approved
0.633	Remote Similarity	NPD5330	Approved
0.633	Remote Similarity	NPD6409	Approved
0.632	Remote Similarity	NPD6274	Approved
0.6316	Remote Similarity	NPD5695	Phase 3
0.6311	Remote Similarity	NPD4634	Approved
0.63	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD7100	Approved
0.6299	Remote Similarity	NPD7101	Approved
0.6293	Remote Similarity	NPD5696	Approved
0.6283	Remote Similarity	NPD5778	Approved
0.6283	Remote Similarity	NPD5779	Approved
0.6271	Remote Similarity	NPD5225	Approved
0.6271	Remote Similarity	NPD4633	Approved
0.6271	Remote Similarity	NPD5226	Approved
0.6271	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD6925	Approved
0.625	Remote Similarity	NPD5776	Phase 2
0.625	Remote Similarity	NPD5357	Phase 1
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD6893	Approved
0.6239	Remote Similarity	NPD1694	Approved
0.622	Remote Similarity	NPD6335	Approved
0.6218	Remote Similarity	NPD5175	Approved
0.6218	Remote Similarity	NPD5174	Approved
0.6216	Remote Similarity	NPD5737	Approved
0.6216	Remote Similarity	NPD6672	Approved
0.6216	Remote Similarity	NPD6903	Approved
0.6214	Remote Similarity	NPD6942	Approved
0.6214	Remote Similarity	NPD7339	Approved
0.6202	Remote Similarity	NPD6908	Approved
0.6202	Remote Similarity	NPD6909	Approved
0.6195	Remote Similarity	NPD7983	Approved
0.6195	Remote Similarity	NPD5693	Phase 1
0.619	Remote Similarity	NPD7145	Approved
0.6186	Remote Similarity	NPD5223	Approved
0.6181	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6902	Approved
0.6168	Remote Similarity	NPD6898	Phase 1
0.6161	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4730	Approved
0.6148	Remote Similarity	NPD4729	Approved
0.6148	Remote Similarity	NPD7260	Phase 2
0.6147	Remote Similarity	NPD3665	Phase 1
0.6147	Remote Similarity	NPD3666	Approved
0.6147	Remote Similarity	NPD4786	Approved
0.6147	Remote Similarity	NPD3133	Approved
0.6142	Remote Similarity	NPD6317	Approved
0.6134	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD3573	Approved
0.6121	Remote Similarity	NPD5221	Approved
0.6121	Remote Similarity	NPD5222	Approved
0.6121	Remote Similarity	NPD4697	Phase 3
0.6121	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6640	Phase 3
0.6111	Remote Similarity	NPD3667	Approved
0.6095	Remote Similarity	NPD6932	Approved
0.6094	Remote Similarity	NPD6313	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