NPASS Compound

Structure

NPC122816 OpenBabel07101718222D 38 41 0 0 1 0 0 0 0 0999 V2000 -6.1472 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -0.3090 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 -6.2812 0.1910 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 -2.6831 0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3171 -2.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 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 -5.2812 1.1910 0.0000 C 0 0 0 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 -6.1472 -1.3090 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 -2.6831 -1.3090 0.0000 C 0 0 2 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 -4.4152 1.6910 0.0000 C 0 0 1 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 -4.4152 -1.3090 0.0000 C 0 0 1 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 -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 -1.8171 -1.8090 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 -7.0132 -1.8090 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 1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3171 -2.6750 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 -1.3578 0.6045 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 -5.2812 -1.8090 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 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 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 34 1 0 0 0 0 9 16 1 0 0 0 0 9 20 1 0 0 0 0 10 19 2 0 0 0 0 10 21 1 0 0 0 0 11 17 1 0 0 0 0 11 26 1 0 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 28 2 0 0 0 0 13 35 1 0 0 0 0 14 29 2 0 0 0 0 14 36 1 0 0 0 0 15 30 2 0 0 0 0 15 37 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 24 1 1 0 0 0 18 22 1 0 0 0 0 18 35 1 6 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 6 0 0 0 20 36 1 0 0 0 0 21 31 2 0 0 0 0 21 38 1 0 0 0 0 22 24 1 6 0 0 0 22 37 1 0 0 0 0 23 27 1 0 0 0 0 24 27 1 1 0 0 0 25 7 1 6 0 0 0 25 32 1 0 0 0 0 26 34 1 6 0 0 0 26 38 1 0 0 0 0 27 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.24
Volume:	524.832
LogP:	2.382
LogD:	1.991
LogS:	-4.056
# Rotatable Bonds:	7
TPSA:	154.89
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	5.482
Fsp3:	0.778
Lipinski Rule-of-5:	Rejected
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:	-5.271
MDCK Permeability:	0.00010248266335111111
Pgp-inhibitor:	0.997
Pgp-substrate:	0.47
Human Intestinal Absorption (HIA):	0.528
20% Bioavailability (F20%):	0.67
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.913
Plasma Protein Binding (PPB):	29.313739776611328%
Volume Distribution (VD):	1.274
Pgp-substrate:	48.58210754394531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.069
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.219
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.277
CYP3A4-substrate:	0.862

ADMET: Excretion

Clearance (CL):	2.575
Half-life (T1/2):	0.649

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.715
Drug-inuced Liver Injury (DILI):	0.839
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.809
Skin Sensitization:	0.725
Carcinogencity:	0.5
Eye Corrosion:	0.006
Eye Irritation:	0.013
Respiratory Toxicity:	0.237

Download Data

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

Natural Product: NPC122816

Natural Product ID:	NPC122816
*Common Name:**	Neocaesalpin W
IUPAC Name:	[(1R,2S,4aR,5S,6aR,7S,10aR,11aS,11bS)-1,2-diacetyloxy-4a,7-dihydroxy-10a-methoxy-4,4,7,11b-tetramethyl-9-oxo-1,2,3,5,6,6a,11,11a-octahydronaphtho[2,1-f][1]benzofuran-5-yl] acetate
Synonyms:
Standard InCHIKey:	GWAJLWJSMZQRPE-FOLDLWRQSA-N
Standard InCHI:	InChI=1S/C27H38O11/c1-13(28)35-18-12-23(4,5)27(33)20(36-14(2)29)9-16-17(24(27,6)22(18)37-15(3)30)11-26(34-8)19(25(16,7)32)10-21(31)38-26/h10,16-18,20,22,32-33H,9,11-12H2,1-8H3/t16-,17+,18+,20+,22+,24+,25+,26-,27-/m1/s1
SMILES:	CC(=O)O[C@H]1CC(C)(C)[C@@]2([C@H](C[C@@H]3[C@H](C[C@@]4(C(=CC(=O)O4)[C@@]3(C)O)OC)[C@@]2(C)[C@H]1OC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386709
PubChem CID:	73350467
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	>	50000.0	nM	PMID[473488]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	47200.0	nM	PMID[473488]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[473488]
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	29100.0	nM	PMID[473488]

☑ 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 NPC122816 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	231
0.1-0.2	1660
0.2-0.3	4648
0.3-0.4	7913
0.4-0.5	13066
0.5-0.6	7529
0.6-0.7	5261
0.7-0.8	2164
0.8-0.85	199
0.85-0.9	17
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC51719
0.96	High Similarity	NPC471205
0.932	High Similarity	NPC177047
0.93	High Similarity	NPC281378
0.8942	High Similarity	NPC181994
0.8942	High Similarity	NPC50124
0.8911	High Similarity	NPC11974
0.8911	High Similarity	NPC472554
0.8857	High Similarity	NPC206618
0.8824	High Similarity	NPC472552
0.8812	High Similarity	NPC38855
0.8762	High Similarity	NPC38948
0.875	High Similarity	NPC471206
0.8738	High Similarity	NPC45897
0.8738	High Similarity	NPC474822
0.8727	High Similarity	NPC83287
0.8636	High Similarity	NPC471354
0.8636	High Similarity	NPC471351
0.8636	High Similarity	NPC152615
0.8636	High Similarity	NPC244402
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	NPC309034
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
0.8627	High Similarity	NPC324841
0.8627	High Similarity	NPC16601
0.8586	High Similarity	NPC7349
0.8571	High Similarity	NPC475136
0.8571	High Similarity	NPC474466
0.8558	High Similarity	NPC120009
0.8558	High Similarity	NPC474575
0.8558	High Similarity	NPC165608
0.8545	High Similarity	NPC193382
0.8545	High Similarity	NPC99620
0.8545	High Similarity	NPC5311
0.8545	High Similarity	NPC199428
0.8545	High Similarity	NPC471816
0.8545	High Similarity	NPC310341
0.8529	High Similarity	NPC325229
0.8529	High Similarity	NPC275086
0.85	High Similarity	NPC105490
0.8485	Intermediate Similarity	NPC329842
0.8482	Intermediate Similarity	NPC329905
0.8468	Intermediate Similarity	NPC93883
0.8462	Intermediate Similarity	NPC109195
0.8462	Intermediate Similarity	NPC11956
0.8462	Intermediate Similarity	NPC472815
0.8462	Intermediate Similarity	NPC475038
0.8462	Intermediate Similarity	NPC121423
0.8455	Intermediate Similarity	NPC471633
0.8455	Intermediate Similarity	NPC31354
0.8455	Intermediate Similarity	NPC84949
0.8455	Intermediate Similarity	NPC69576
0.8431	Intermediate Similarity	NPC199099
0.8431	Intermediate Similarity	NPC51499
0.8421	Intermediate Similarity	NPC264336
0.8416	Intermediate Similarity	NPC276110
0.8411	Intermediate Similarity	NPC88701
0.8407	Intermediate Similarity	NPC475629
0.8407	Intermediate Similarity	NPC475556
0.84	Intermediate Similarity	NPC110022
0.84	Intermediate Similarity	NPC472640
0.84	Intermediate Similarity	NPC472641
0.8396	Intermediate Similarity	NPC477090
0.8381	Intermediate Similarity	NPC23584
0.8381	Intermediate Similarity	NPC473523
0.8365	Intermediate Similarity	NPC477717
0.8333	Intermediate Similarity	NPC475030
0.8333	Intermediate Similarity	NPC40749
0.8333	Intermediate Similarity	NPC194132
0.8333	Intermediate Similarity	NPC314535
0.8333	Intermediate Similarity	NPC173555
0.8319	Intermediate Similarity	NPC29639
0.8319	Intermediate Similarity	NPC32177
0.8319	Intermediate Similarity	NPC55532
0.8319	Intermediate Similarity	NPC30483
0.8319	Intermediate Similarity	NPC44899
0.8319	Intermediate Similarity	NPC304260
0.8319	Intermediate Similarity	NPC470897
0.8319	Intermediate Similarity	NPC292467
0.8319	Intermediate Similarity	NPC5883
0.8319	Intermediate Similarity	NPC236973
0.8319	Intermediate Similarity	NPC469756
0.8318	Intermediate Similarity	NPC472820
0.8318	Intermediate Similarity	NPC67321
0.8318	Intermediate Similarity	NPC187435
0.8318	Intermediate Similarity	NPC473586
0.8317	Intermediate Similarity	NPC140277
0.8304	Intermediate Similarity	NPC290693
0.8304	Intermediate Similarity	NPC203862
0.8302	Intermediate Similarity	NPC473543
0.8302	Intermediate Similarity	NPC471937
0.83	Intermediate Similarity	NPC78594
0.8286	Intermediate Similarity	NPC214277
0.8273	Intermediate Similarity	NPC473125
0.8273	Intermediate Similarity	NPC470025
0.8273	Intermediate Similarity	NPC321272
0.8273	Intermediate Similarity	NPC328074
0.8273	Intermediate Similarity	NPC317460
0.8269	Intermediate Similarity	NPC477716
0.8269	Intermediate Similarity	NPC477721
0.8269	Intermediate Similarity	NPC188968
0.8246	Intermediate Similarity	NPC72260
0.8241	Intermediate Similarity	NPC475263
0.8235	Intermediate Similarity	NPC471915
0.823	Intermediate Similarity	NPC218093
0.8224	Intermediate Similarity	NPC186668
0.8224	Intermediate Similarity	NPC472818
0.8224	Intermediate Similarity	NPC239961
0.8218	Intermediate Similarity	NPC53555
0.8208	Intermediate Similarity	NPC471938
0.8208	Intermediate Similarity	NPC189588
0.8208	Intermediate Similarity	NPC187302
0.8208	Intermediate Similarity	NPC97487
0.8208	Intermediate Similarity	NPC10232
0.8208	Intermediate Similarity	NPC474124
0.8208	Intermediate Similarity	NPC196471
0.8208	Intermediate Similarity	NPC160583
0.8208	Intermediate Similarity	NPC472821
0.82	Intermediate Similarity	NPC472642
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	NPC264153
0.8198	Intermediate Similarity	NPC473159
0.8198	Intermediate Similarity	NPC470027
0.819	Intermediate Similarity	NPC235920
0.819	Intermediate Similarity	NPC117445
0.819	Intermediate Similarity	NPC208193
0.819	Intermediate Similarity	NPC198992
0.819	Intermediate Similarity	NPC475617
0.819	Intermediate Similarity	NPC308262
0.819	Intermediate Similarity	NPC96784
0.819	Intermediate Similarity	NPC280991
0.8182	Intermediate Similarity	NPC17791
0.8174	Intermediate Similarity	NPC475419
0.8174	Intermediate Similarity	NPC120390
0.8174	Intermediate Similarity	NPC231518
0.8174	Intermediate Similarity	NPC475219
0.8174	Intermediate Similarity	NPC475590
0.8174	Intermediate Similarity	NPC474908
0.8173	Intermediate Similarity	NPC278673
0.8165	Intermediate Similarity	NPC473570
0.8165	Intermediate Similarity	NPC299590
0.8165	Intermediate Similarity	NPC475586
0.8158	Intermediate Similarity	NPC291820
0.8158	Intermediate Similarity	NPC81222
0.8158	Intermediate Similarity	NPC153085
0.8158	Intermediate Similarity	NPC470914
0.8158	Intermediate Similarity	NPC268326
0.8155	Intermediate Similarity	NPC90583
0.8155	Intermediate Similarity	NPC165632
0.8155	Intermediate Similarity	NPC209297
0.8155	Intermediate Similarity	NPC472995
0.8155	Intermediate Similarity	NPC475380
0.8148	Intermediate Similarity	NPC475074
0.8148	Intermediate Similarity	NPC472390
0.8142	Intermediate Similarity	NPC473968
0.8142	Intermediate Similarity	NPC474483
0.8131	Intermediate Similarity	NPC472819
0.8113	Intermediate Similarity	NPC470571
0.8113	Intermediate Similarity	NPC471914
0.8113	Intermediate Similarity	NPC475344
0.8113	Intermediate Similarity	NPC476471
0.8113	Intermediate Similarity	NPC470053
0.8113	Intermediate Similarity	NPC150463
0.8108	Intermediate Similarity	NPC42658
0.8103	Intermediate Similarity	NPC74259
0.8103	Intermediate Similarity	NPC196130
0.8103	Intermediate Similarity	NPC474423
0.8103	Intermediate Similarity	NPC193893
0.8103	Intermediate Similarity	NPC115349
0.8095	Intermediate Similarity	NPC272223
0.8095	Intermediate Similarity	NPC230546
0.8095	Intermediate Similarity	NPC79303
0.8095	Intermediate Similarity	NPC271295
0.8091	Intermediate Similarity	NPC316708
0.8087	Intermediate Similarity	NPC107607
0.8087	Intermediate Similarity	NPC470312
0.8087	Intermediate Similarity	NPC135369
0.8077	Intermediate Similarity	NPC274793
0.8077	Intermediate Similarity	NPC473244
0.8077	Intermediate Similarity	NPC475446
0.8077	Intermediate Similarity	NPC100912
0.8077	Intermediate Similarity	NPC311241

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 NPC122816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1842
0.2-0.3	3870
0.3-0.4	2118
0.4-0.5	695
0.5-0.6	304
0.6-0.7	101
0.7-0.8	20
0.8-0.85	8
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	NPD8378	Approved
0.8333	Intermediate Similarity	NPD8296	Approved
0.8333	Intermediate Similarity	NPD8335	Approved
0.8333	Intermediate Similarity	NPD8379	Approved
0.8333	Intermediate Similarity	NPD8380	Approved
0.8246	Intermediate Similarity	NPD8377	Approved
0.8246	Intermediate Similarity	NPD8294	Approved
0.8174	Intermediate Similarity	NPD8033	Approved
0.8165	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD6686	Approved
0.7925	Intermediate Similarity	NPD7639	Approved
0.7925	Intermediate Similarity	NPD7640	Approved
0.7899	Intermediate Similarity	NPD7507	Approved
0.7851	Intermediate Similarity	NPD7319	Approved
0.785	Intermediate Similarity	NPD5344	Discontinued
0.783	Intermediate Similarity	NPD7638	Approved
0.7818	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7503	Approved
0.7593	Intermediate Similarity	NPD6648	Approved
0.75	Intermediate Similarity	NPD4225	Approved
0.7455	Intermediate Similarity	NPD7632	Discontinued
0.7281	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8133	Approved
0.7217	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7115	Discovery
0.7043	Intermediate Similarity	NPD6412	Phase 2
0.7016	Intermediate Similarity	NPD8328	Phase 3
0.6891	Remote Similarity	NPD6882	Approved
0.6887	Remote Similarity	NPD7524	Approved
0.6875	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7492	Approved
0.6818	Remote Similarity	NPD7748	Approved
0.6812	Remote Similarity	NPD7625	Phase 1
0.6803	Remote Similarity	NPD6009	Approved
0.6803	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7736	Approved
0.6786	Remote Similarity	NPD7902	Approved
0.6774	Remote Similarity	NPD6319	Approved
0.6774	Remote Similarity	NPD6059	Approved
0.6774	Remote Similarity	NPD6054	Approved
0.6772	Remote Similarity	NPD6616	Approved
0.6762	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8297	Approved
0.672	Remote Similarity	NPD8517	Approved
0.672	Remote Similarity	NPD8516	Approved
0.672	Remote Similarity	NPD8513	Phase 3
0.672	Remote Similarity	NPD8515	Approved
0.672	Remote Similarity	NPD6921	Approved
0.6719	Remote Similarity	NPD8293	Discontinued
0.6719	Remote Similarity	NPD7078	Approved
0.6699	Remote Similarity	NPD7525	Registered
0.6697	Remote Similarity	NPD6698	Approved
0.6697	Remote Similarity	NPD46	Approved
0.6697	Remote Similarity	NPD7838	Discovery
0.6694	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD6372	Approved
0.6639	Remote Similarity	NPD6373	Approved
0.6636	Remote Similarity	NPD7515	Phase 2
0.6606	Remote Similarity	NPD6051	Approved
0.6604	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6015	Approved
0.6587	Remote Similarity	NPD6016	Approved
0.6571	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6899	Approved
0.6555	Remote Similarity	NPD6881	Approved
0.6555	Remote Similarity	NPD7320	Approved
0.6545	Remote Similarity	NPD3168	Discontinued
0.6535	Remote Similarity	NPD5988	Approved
0.6529	Remote Similarity	NPD6649	Approved
0.6529	Remote Similarity	NPD6650	Approved
0.6518	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD7900	Approved
0.6509	Remote Similarity	NPD6695	Phase 3
0.6486	Remote Similarity	NPD7637	Suspended
0.6471	Remote Similarity	NPD5697	Approved
0.6471	Remote Similarity	NPD5701	Approved
0.6466	Remote Similarity	NPD4159	Approved
0.6465	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8074	Phase 3
0.6446	Remote Similarity	NPD6883	Approved
0.6446	Remote Similarity	NPD7290	Approved
0.6446	Remote Similarity	NPD6371	Approved
0.6446	Remote Similarity	NPD7102	Approved
0.6442	Remote Similarity	NPD7645	Phase 2
0.6429	Remote Similarity	NPD6399	Phase 3
0.6393	Remote Similarity	NPD8130	Phase 1
0.6393	Remote Similarity	NPD6617	Approved
0.6393	Remote Similarity	NPD6847	Approved
0.6393	Remote Similarity	NPD6869	Approved
0.6387	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD6013	Approved
0.6364	Remote Similarity	NPD6012	Approved
0.6357	Remote Similarity	NPD7604	Phase 2
0.6357	Remote Similarity	NPD6067	Discontinued
0.6348	Remote Similarity	NPD6083	Phase 2
0.6348	Remote Similarity	NPD6084	Phase 2
0.6341	Remote Similarity	NPD6053	Discontinued
0.6339	Remote Similarity	NPD8035	Phase 2
0.6339	Remote Similarity	NPD8034	Phase 2
0.6333	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD5983	Phase 2
0.6288	Remote Similarity	NPD6033	Approved
0.6281	Remote Similarity	NPD6011	Approved
0.6273	Remote Similarity	NPD7750	Discontinued
0.6271	Remote Similarity	NPD5211	Phase 2
0.626	Remote Similarity	NPD6336	Discontinued
0.626	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD1694	Approved
0.6226	Remote Similarity	NPD6931	Approved
0.6226	Remote Similarity	NPD6930	Phase 2
0.6216	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4755	Approved
0.6182	Remote Similarity	NPD7334	Approved
0.6182	Remote Similarity	NPD3618	Phase 1
0.6182	Remote Similarity	NPD7146	Approved
0.6182	Remote Similarity	NPD6684	Approved
0.6182	Remote Similarity	NPD6409	Approved
0.6182	Remote Similarity	NPD5330	Approved
0.6182	Remote Similarity	NPD7521	Approved
0.6179	Remote Similarity	NPD4634	Approved
0.6174	Remote Similarity	NPD5695	Phase 3
0.6167	Remote Similarity	NPD5141	Approved
0.6161	Remote Similarity	NPD5328	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.614	Remote Similarity	NPD8171	Discontinued
0.614	Remote Similarity	NPD4202	Approved
0.6132	Remote Similarity	NPD6929	Approved
0.6126	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5357	Phase 1
0.6102	Remote Similarity	NPD5286	Approved
0.6102	Remote Similarity	NPD4700	Approved
0.6102	Remote Similarity	NPD5285	Approved
0.6102	Remote Similarity	NPD4696	Approved
0.6091	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7514	Phase 3
0.6075	Remote Similarity	NPD7332	Phase 2
0.6071	Remote Similarity	NPD6672	Approved
0.6071	Remote Similarity	NPD6903	Approved
0.6071	Remote Similarity	NPD5737	Approved
0.6069	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6274	Approved
0.6055	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD3669	Approved
0.6053	Remote Similarity	NPD6079	Approved
0.6053	Remote Similarity	NPD7087	Discontinued
0.6053	Remote Similarity	NPD5693	Phase 1
0.6053	Remote Similarity	NPD7983	Approved
0.6047	Remote Similarity	NPD7101	Approved
0.6047	Remote Similarity	NPD7100	Approved
0.6034	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD5778	Approved
0.6	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6640	Phase 3
0.5984	Remote Similarity	NPD4767	Approved
0.5984	Remote Similarity	NPD4768	Approved
0.5982	Remote Similarity	NPD3573	Approved
0.5969	Remote Similarity	NPD6335	Approved
0.5954	Remote Similarity	NPD6908	Approved
0.5954	Remote Similarity	NPD6909	Approved
0.595	Remote Similarity	NPD5175	Approved
0.595	Remote Similarity	NPD5174	Approved
0.5946	Remote Similarity	NPD6893	Approved
0.5943	Remote Similarity	NPD6925	Approved
0.5943	Remote Similarity	NPD5776	Phase 2
0.5926	Remote Similarity	NPD6928	Phase 2
0.5917	Remote Similarity	NPD5223	Approved
0.5905	Remote Similarity	NPD6942	Approved
0.5905	Remote Similarity	NPD7339	Approved
0.5902	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD4623	Approved
0.5893	Remote Similarity	NPD4519	Discontinued
0.5893	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6317	Approved
0.5888	Remote Similarity	NPD7145	Approved
0.5888	Remote Similarity	NPD6118	Approved
0.5888	Remote Similarity	NPD6697	Approved
0.5888	Remote Similarity	NPD6115	Approved
0.5888	Remote Similarity	NPD6114	Approved
0.5887	Remote Similarity	NPD4730	Approved
0.5887	Remote Similarity	NPD4729	Approved
0.5882	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6904	Approved
0.5877	Remote Similarity	NPD7285	Clinical (unspecified phase)

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