NPASS Compound

Structure

CID305496 OpenBabel06191716112D 36 43 0 0 1 0 0 0 0 0999 V2000 1.6199 1.5441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4042 -0.7580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5701 0.7068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6017 -0.9488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5656 -1.5787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9456 -1.2421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1001 -1.7302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7192 3.1495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9459 -0.2663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1258 2.6617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2552 1.6859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5647 -0.2664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6780 1.1745 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4097 1.1978 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5642 1.6860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4097 0.2215 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2549 -1.2426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1007 1.1977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6218 0.4240 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4980 -0.0819 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0993 -0.4222 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2552 -0.2667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7192 1.1982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6038 -1.0881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5935 -1.2985 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1263 1.6864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1007 0.2214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7192 0.2218 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4039 -1.7338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1056 -0.3165 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9773 2.1777 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7192 -0.7608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4223 0.3296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9462 0.7096 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 1.9165 -2.0504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 10 26 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 28 1 0 0 0 0 13 19 1 0 0 0 0 13 26 1 6 0 0 0 14 11 1 1 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 23 1 6 0 0 0 16 22 1 6 0 0 0 17 22 1 0 0 0 0 17 29 2 0 0 0 0 18 27 1 6 0 0 0 18 34 1 0 0 0 0 19 20 1 0 0 0 0 19 35 1 1 0 0 0 20 24 1 6 0 0 0 20 33 1 0 0 0 0 21 25 1 6 0 0 0 21 30 1 0 0 0 0 21 33 1 0 0 0 0 22 27 1 6 0 0 0 23 26 1 6 0 0 0 24 25 1 6 0 0 0 24 36 1 0 0 0 0 25 5 1 6 0 0 0 25 36 1 0 0 0 0 26 31 1 6 0 0 0 27 9 1 1 0 0 0 27 34 1 0 0 0 0 28 23 1 6 0 0 0 28 32 1 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.26
Volume:	489.441
LogP:	2.511
LogD:	1.998
LogS:	-4.601
# Rotatable Bonds:	1
TPSA:	121.28
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	6.643
Fsp3:	0.893
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:	-5.375
MDCK Permeability:	3.513416595524177e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.654
30% Bioavailability (F30%):	0.873

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.727
Plasma Protein Binding (PPB):	20.791690826416016%
Volume Distribution (VD):	0.563
Pgp-substrate:	45.230438232421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.994
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.842

ADMET: Excretion

Clearance (CL):	11.31
Half-life (T1/2):	0.55

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.303
Drug-inuced Liver Injury (DILI):	0.123
AMES Toxicity:	0.571
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.577
Skin Sensitization:	0.853
Carcinogencity:	0.943
Eye Corrosion:	0.011
Eye Irritation:	0.022
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC305496

Natural Product ID:	NPC305496
*Common Name:**	Jaborosalactol 24
IUPAC Name:	n.a.
Synonyms:	Jaborosalactol 24
Standard InCHIKey:	IBPQMXUWLQVNBJ-UIEXBFMASA-N
Standard InCHI:	InChI=1S/C28H38O8/c1-13-19(20-24(4)25(5,36-24)21(30)33-20)35-28(32)12-16-14(15-8-10-26(13,31)23(15,28)3)11-18-27(34-18)9-6-7-17(29)22(16,27)2/h6-7,13-16,18-21,30-32H,8-12H2,1-5H3/t13-,14+,15+,16+,18-,19+,20+,21+,22+,23+,24+,25-,26-,27-,28+/m1/s1
SMILES:	C[C@@H]1[C@@H]([C@H]2[C@@]3(C)[C@@](C)([C@@H](O)O2)O3)O[C@]2(C[C@H]3[C@@H](C[C@@H]4[C@@]5(CC=CC(=O)[C@]35C)O4)[C@@H]3CC[C@@]1([C@@]23C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094364
PubChem CID:	46888732
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO12110	Bauhinia tarapotensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473417]
NPO5120	Betula nana	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12110	Bauhinia tarapotensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11613	Pelea barbigera	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19839	Pimpinella acuminata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11863	Achromobacter cycloclastes	Species	Alcaligenaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9504	Thyone aurea	Species	Phyllophoridae	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
GI50	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
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	8700.0	nM	PMID[571065]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	3600.0	nM	PMID[571065]
NPT396	Cell Line	T47D	Homo sapiens	GI50	=	6500.0	nM	PMID[571065]
NPT134	Cell Line	SK-BR-3	Homo sapiens	GI50	=	2300.0	nM	PMID[571065]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	2600.0	nM	PMID[571065]

☑ 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 NPC305496 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	310
0.1-0.2	1900
0.2-0.3	5835
0.3-0.4	9975
0.4-0.5	11092
0.5-0.6	6744
0.6-0.7	4840
0.7-0.8	1891
0.8-0.85	94
0.85-0.9	14
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9098	High Similarity	NPC473620
0.8934	High Similarity	NPC47113
0.8934	High Similarity	NPC174367
0.8908	High Similarity	NPC473203
0.8803	High Similarity	NPC471173
0.8803	High Similarity	NPC471627
0.874	High Similarity	NPC198361
0.872	High Similarity	NPC470880
0.871	High Similarity	NPC287423
0.871	High Similarity	NPC473253
0.8699	High Similarity	NPC473255
0.8655	High Similarity	NPC302471
0.864	High Similarity	NPC311534
0.8595	High Similarity	NPC61520
0.8571	High Similarity	NPC473593
0.856	High Similarity	NPC473265
0.856	High Similarity	NPC470882
0.856	High Similarity	NPC42399
0.8537	High Similarity	NPC28532
0.8525	High Similarity	NPC241192
0.8512	High Similarity	NPC329736
0.8487	Intermediate Similarity	NPC178981
0.8487	Intermediate Similarity	NPC260665
0.8475	Intermediate Similarity	NPC471243
0.8455	Intermediate Similarity	NPC473256
0.8455	Intermediate Similarity	NPC470878
0.8443	Intermediate Similarity	NPC161065
0.8443	Intermediate Similarity	NPC161738
0.8438	Intermediate Similarity	NPC471855
0.8438	Intermediate Similarity	NPC231240
0.843	Intermediate Similarity	NPC218970
0.8417	Intermediate Similarity	NPC471398
0.8417	Intermediate Similarity	NPC243354
0.8417	Intermediate Similarity	NPC477580
0.84	Intermediate Similarity	NPC8374
0.84	Intermediate Similarity	NPC475194
0.84	Intermediate Similarity	NPC8369
0.84	Intermediate Similarity	NPC473505
0.8372	Intermediate Similarity	NPC316915
0.8361	Intermediate Similarity	NPC473720
0.8361	Intermediate Similarity	NPC475632
0.8361	Intermediate Similarity	NPC86020
0.8359	Intermediate Similarity	NPC173347
0.8347	Intermediate Similarity	NPC270929
0.8346	Intermediate Similarity	NPC168899
0.8346	Intermediate Similarity	NPC473888
0.8346	Intermediate Similarity	NPC69273
0.8346	Intermediate Similarity	NPC293623
0.8333	Intermediate Similarity	NPC225049
0.8333	Intermediate Similarity	NPC477944
0.8333	Intermediate Similarity	NPC93368
0.832	Intermediate Similarity	NPC238005
0.832	Intermediate Similarity	NPC204812
0.832	Intermediate Similarity	NPC469789
0.832	Intermediate Similarity	NPC1980
0.832	Intermediate Similarity	NPC141196
0.8308	Intermediate Similarity	NPC471234
0.8306	Intermediate Similarity	NPC182900
0.8306	Intermediate Similarity	NPC249553
0.8306	Intermediate Similarity	NPC477046
0.8306	Intermediate Similarity	NPC102822
0.8293	Intermediate Similarity	NPC473274
0.8293	Intermediate Similarity	NPC469488
0.8293	Intermediate Similarity	NPC319570
0.8281	Intermediate Similarity	NPC471407
0.8281	Intermediate Similarity	NPC476966
0.8281	Intermediate Similarity	NPC231529
0.8268	Intermediate Similarity	NPC117702
0.8268	Intermediate Similarity	NPC469757
0.8268	Intermediate Similarity	NPC471357
0.8268	Intermediate Similarity	NPC298841
0.8268	Intermediate Similarity	NPC146456
0.8264	Intermediate Similarity	NPC74727
0.8254	Intermediate Similarity	NPC32868
0.8254	Intermediate Similarity	NPC241456
0.825	Intermediate Similarity	NPC471244
0.825	Intermediate Similarity	NPC471245
0.825	Intermediate Similarity	NPC205534
0.824	Intermediate Similarity	NPC313528
0.824	Intermediate Similarity	NPC15918
0.824	Intermediate Similarity	NPC23786
0.824	Intermediate Similarity	NPC153700
0.824	Intermediate Similarity	NPC470265
0.824	Intermediate Similarity	NPC305771
0.824	Intermediate Similarity	NPC169816
0.824	Intermediate Similarity	NPC475431
0.824	Intermediate Similarity	NPC94072
0.824	Intermediate Similarity	NPC88326
0.8235	Intermediate Similarity	NPC52241
0.8235	Intermediate Similarity	NPC475317
0.8235	Intermediate Similarity	NPC473324
0.8235	Intermediate Similarity	NPC154856
0.8235	Intermediate Similarity	NPC471476
0.8226	Intermediate Similarity	NPC471406
0.8226	Intermediate Similarity	NPC475187
0.8217	Intermediate Similarity	NPC241008
0.8211	Intermediate Similarity	NPC239293
0.8211	Intermediate Similarity	NPC297179
0.8203	Intermediate Similarity	NPC245094
0.8197	Intermediate Similarity	NPC243981
0.8197	Intermediate Similarity	NPC88945
0.8189	Intermediate Similarity	NPC293112
0.8189	Intermediate Similarity	NPC473635
0.8189	Intermediate Similarity	NPC198714
0.8182	Intermediate Similarity	NPC255017
0.8182	Intermediate Similarity	NPC52634
0.8182	Intermediate Similarity	NPC194273
0.8182	Intermediate Similarity	NPC317210
0.8182	Intermediate Similarity	NPC320118
0.8182	Intermediate Similarity	NPC132668
0.8175	Intermediate Similarity	NPC11895
0.8175	Intermediate Similarity	NPC27363
0.8168	Intermediate Similarity	NPC478072
0.8167	Intermediate Similarity	NPC63244
0.8167	Intermediate Similarity	NPC474229
0.8167	Intermediate Similarity	NPC122339
0.816	Intermediate Similarity	NPC67569
0.816	Intermediate Similarity	NPC42675
0.816	Intermediate Similarity	NPC202051
0.8151	Intermediate Similarity	NPC246205
0.8145	Intermediate Similarity	NPC473270
0.8145	Intermediate Similarity	NPC476960
0.8145	Intermediate Similarity	NPC475520
0.814	Intermediate Similarity	NPC86159
0.814	Intermediate Similarity	NPC469755
0.814	Intermediate Similarity	NPC469753
0.814	Intermediate Similarity	NPC10823
0.814	Intermediate Similarity	NPC471352
0.814	Intermediate Similarity	NPC180079
0.814	Intermediate Similarity	NPC251866
0.814	Intermediate Similarity	NPC284406
0.814	Intermediate Similarity	NPC17896
0.814	Intermediate Similarity	NPC70542
0.814	Intermediate Similarity	NPC89514
0.814	Intermediate Similarity	NPC471361
0.814	Intermediate Similarity	NPC9499
0.814	Intermediate Similarity	NPC6108
0.814	Intermediate Similarity	NPC469751
0.814	Intermediate Similarity	NPC219085
0.814	Intermediate Similarity	NPC469754
0.814	Intermediate Similarity	NPC471360
0.814	Intermediate Similarity	NPC469752
0.814	Intermediate Similarity	NPC471359
0.814	Intermediate Similarity	NPC197707
0.814	Intermediate Similarity	NPC471358
0.813	Intermediate Similarity	NPC473304
0.8125	Intermediate Similarity	NPC152091
0.8115	Intermediate Similarity	NPC326542
0.811	Intermediate Similarity	NPC469790
0.811	Intermediate Similarity	NPC190846
0.811	Intermediate Similarity	NPC172154
0.811	Intermediate Similarity	NPC277191
0.811	Intermediate Similarity	NPC81736
0.8099	Intermediate Similarity	NPC473303
0.8099	Intermediate Similarity	NPC210420
0.8099	Intermediate Similarity	NPC474265
0.8099	Intermediate Similarity	NPC207251
0.8099	Intermediate Similarity	NPC130427
0.8099	Intermediate Similarity	NPC474927
0.8095	Intermediate Similarity	NPC216866
0.8095	Intermediate Similarity	NPC269642
0.8095	Intermediate Similarity	NPC65858
0.8095	Intermediate Similarity	NPC170538
0.8095	Intermediate Similarity	NPC156789
0.8092	Intermediate Similarity	NPC475487
0.8083	Intermediate Similarity	NPC470065
0.808	Intermediate Similarity	NPC474370
0.808	Intermediate Similarity	NPC476961
0.8067	Intermediate Similarity	NPC189663
0.8067	Intermediate Similarity	NPC272576
0.8067	Intermediate Similarity	NPC55973
0.8067	Intermediate Similarity	NPC89860
0.8065	Intermediate Similarity	NPC118638
0.8065	Intermediate Similarity	NPC204552
0.8065	Intermediate Similarity	NPC188667
0.8051	Intermediate Similarity	NPC470309
0.8049	Intermediate Similarity	NPC134869
0.8049	Intermediate Similarity	NPC49492
0.8049	Intermediate Similarity	NPC266728
0.8049	Intermediate Similarity	NPC235539
0.8049	Intermediate Similarity	NPC152199
0.8047	Intermediate Similarity	NPC250556
0.8047	Intermediate Similarity	NPC104427
0.8047	Intermediate Similarity	NPC469750
0.8033	Intermediate Similarity	NPC94141
0.8033	Intermediate Similarity	NPC293038
0.8033	Intermediate Similarity	NPC194100
0.8033	Intermediate Similarity	NPC471252
0.8033	Intermediate Similarity	NPC62696
0.8033	Intermediate Similarity	NPC102619
0.8031	Intermediate Similarity	NPC43252
0.8031	Intermediate Similarity	NPC160084
0.8031	Intermediate Similarity	NPC135038
0.8017	Intermediate Similarity	NPC213320
0.8016	Intermediate Similarity	NPC470921
0.8016	Intermediate Similarity	NPC475182
0.8016	Intermediate Similarity	NPC46570
0.8016	Intermediate Similarity	NPC204731
0.8015	Intermediate Similarity	NPC254614
0.8015	Intermediate Similarity	NPC33378

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 NPC305496 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	2109
0.2-0.3	4166
0.3-0.4	1702
0.4-0.5	459
0.5-0.6	257
0.6-0.7	131
0.7-0.8	60
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8689	High Similarity	NPD6370	Approved
0.8525	High Similarity	NPD6054	Approved
0.8492	Intermediate Similarity	NPD7736	Approved
0.8306	Intermediate Similarity	NPD6016	Approved
0.8306	Intermediate Similarity	NPD6015	Approved
0.8254	Intermediate Similarity	NPD7492	Approved
0.824	Intermediate Similarity	NPD5988	Approved
0.8226	Intermediate Similarity	NPD6059	Approved
0.8189	Intermediate Similarity	NPD6616	Approved
0.814	Intermediate Similarity	NPD7319	Approved
0.8136	Intermediate Similarity	NPD6412	Phase 2
0.8125	Intermediate Similarity	NPD7078	Approved
0.8125	Intermediate Similarity	NPD8293	Discontinued
0.808	Intermediate Similarity	NPD6319	Approved
0.8047	Intermediate Similarity	NPD7507	Approved
0.7899	Intermediate Similarity	NPD6008	Approved
0.784	Intermediate Similarity	NPD7115	Discovery
0.7805	Intermediate Similarity	NPD8297	Approved
0.7805	Intermediate Similarity	NPD6882	Approved
0.7787	Intermediate Similarity	NPD4634	Approved
0.7752	Intermediate Similarity	NPD8328	Phase 3
0.7742	Intermediate Similarity	NPD4632	Approved
0.7724	Intermediate Similarity	NPD6650	Approved
0.7724	Intermediate Similarity	NPD6649	Approved
0.7698	Intermediate Similarity	NPD6009	Approved
0.7652	Intermediate Similarity	NPD6033	Approved
0.7623	Intermediate Similarity	NPD6899	Approved
0.7623	Intermediate Similarity	NPD6881	Approved
0.7561	Intermediate Similarity	NPD6373	Approved
0.7561	Intermediate Similarity	NPD6372	Approved
0.7541	Intermediate Similarity	NPD5697	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.7481	Intermediate Similarity	NPD7604	Phase 2
0.748	Intermediate Similarity	NPD7320	Approved
0.7479	Intermediate Similarity	NPD5285	Approved
0.7479	Intermediate Similarity	NPD5286	Approved
0.7479	Intermediate Similarity	NPD4696	Approved
0.7462	Intermediate Similarity	NPD7503	Approved
0.7462	Intermediate Similarity	NPD8033	Approved
0.7459	Intermediate Similarity	NPD6675	Approved
0.7459	Intermediate Similarity	NPD6402	Approved
0.7459	Intermediate Similarity	NPD7128	Approved
0.7459	Intermediate Similarity	NPD5739	Approved
0.7442	Intermediate Similarity	NPD7516	Approved
0.744	Intermediate Similarity	NPD6869	Approved
0.744	Intermediate Similarity	NPD8130	Phase 1
0.744	Intermediate Similarity	NPD6847	Approved
0.744	Intermediate Similarity	NPD6617	Approved
0.7422	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6012	Approved
0.7419	Intermediate Similarity	NPD6013	Approved
0.7419	Intermediate Similarity	NPD6014	Approved
0.7385	Intermediate Similarity	NPD8294	Approved
0.7385	Intermediate Similarity	NPD8377	Approved
0.7377	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5224	Approved
0.7355	Intermediate Similarity	NPD5211	Phase 2
0.7355	Intermediate Similarity	NPD5225	Approved
0.7355	Intermediate Similarity	NPD4633	Approved
0.7355	Intermediate Similarity	NPD5226	Approved
0.7348	Intermediate Similarity	NPD6067	Discontinued
0.7339	Intermediate Similarity	NPD6011	Approved
0.7328	Intermediate Similarity	NPD8335	Approved
0.7328	Intermediate Similarity	NPD5983	Phase 2
0.7328	Intermediate Similarity	NPD8378	Approved
0.7328	Intermediate Similarity	NPD8296	Approved
0.7328	Intermediate Similarity	NPD8380	Approved
0.7328	Intermediate Similarity	NPD8379	Approved
0.7311	Intermediate Similarity	NPD4755	Approved
0.7295	Intermediate Similarity	NPD5174	Approved
0.7295	Intermediate Similarity	NPD5175	Approved
0.728	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5223	Approved
0.7258	Intermediate Similarity	NPD5701	Approved
0.7239	Intermediate Similarity	NPD6336	Discontinued
0.7236	Intermediate Similarity	NPD5141	Approved
0.72	Intermediate Similarity	NPD4730	Approved
0.72	Intermediate Similarity	NPD6686	Approved
0.72	Intermediate Similarity	NPD4729	Approved
0.7197	Intermediate Similarity	NPD8513	Phase 3
0.7197	Intermediate Similarity	NPD8517	Approved
0.7197	Intermediate Similarity	NPD8516	Approved
0.7197	Intermediate Similarity	NPD8515	Approved
0.719	Intermediate Similarity	NPD4700	Approved
0.7179	Intermediate Similarity	NPD6079	Approved
0.7153	Intermediate Similarity	NPD5956	Approved
0.7087	Intermediate Similarity	NPD5248	Approved
0.7087	Intermediate Similarity	NPD5250	Approved
0.7087	Intermediate Similarity	NPD5249	Phase 3
0.7087	Intermediate Similarity	NPD5247	Approved
0.7087	Intermediate Similarity	NPD5251	Approved
0.7068	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD8133	Approved
0.7045	Intermediate Similarity	NPD7100	Approved
0.7045	Intermediate Similarity	NPD7101	Approved
0.704	Intermediate Similarity	NPD4767	Approved
0.704	Intermediate Similarity	NPD4768	Approved
0.7031	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5328	Approved
0.7008	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4202	Approved
0.697	Remote Similarity	NPD6335	Approved
0.6953	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6274	Approved
0.6942	Remote Similarity	NPD5221	Approved
0.6942	Remote Similarity	NPD5222	Approved
0.6942	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5128	Approved
0.6899	Remote Similarity	NPD5215	Approved
0.6899	Remote Similarity	NPD5217	Approved
0.6899	Remote Similarity	NPD5216	Approved
0.6894	Remote Similarity	NPD6317	Approved
0.6885	Remote Similarity	NPD5173	Approved
0.6885	Remote Similarity	NPD6083	Phase 2
0.6885	Remote Similarity	NPD6084	Phase 2
0.688	Remote Similarity	NPD4754	Approved
0.686	Remote Similarity	NPD4629	Approved
0.686	Remote Similarity	NPD5210	Approved
0.6842	Remote Similarity	NPD6313	Approved
0.6842	Remote Similarity	NPD6314	Approved
0.6833	Remote Similarity	NPD6399	Phase 3
0.6822	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5169	Approved
0.6822	Remote Similarity	NPD5135	Approved
0.6803	Remote Similarity	NPD4697	Phase 3
0.6777	Remote Similarity	NPD6001	Approved
0.6769	Remote Similarity	NPD5127	Approved
0.6752	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD3618	Phase 1
0.6723	Remote Similarity	NPD4753	Phase 2
0.6719	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6053	Discontinued
0.6694	Remote Similarity	NPD7638	Approved
0.6694	Remote Similarity	NPD4225	Approved
0.6694	Remote Similarity	NPD5696	Approved
0.6692	Remote Similarity	NPD6371	Approved
0.6691	Remote Similarity	NPD6909	Approved
0.6691	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD4522	Approved
0.6646	Remote Similarity	NPD7799	Discontinued
0.664	Remote Similarity	NPD7640	Approved
0.664	Remote Similarity	NPD7639	Approved
0.6639	Remote Similarity	NPD5282	Discontinued
0.6617	Remote Similarity	NPD5167	Approved
0.6613	Remote Similarity	NPD7902	Approved
0.6589	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5695	Phase 3
0.6581	Remote Similarity	NPD3133	Approved
0.6581	Remote Similarity	NPD3666	Approved
0.6581	Remote Similarity	NPD4786	Approved
0.6581	Remote Similarity	NPD3665	Phase 1
0.6575	Remote Similarity	NPD6334	Approved
0.6575	Remote Similarity	NPD6333	Approved
0.6573	Remote Similarity	NPD8338	Approved
0.6571	Remote Similarity	NPD8074	Phase 3
0.6569	Remote Similarity	NPD6921	Approved
0.6567	Remote Similarity	NPD6868	Approved
0.6557	Remote Similarity	NPD8171	Discontinued
0.6555	Remote Similarity	NPD3573	Approved
0.6525	Remote Similarity	NPD8336	Approved
0.6525	Remote Similarity	NPD8337	Approved
0.6504	Remote Similarity	NPD7748	Approved
0.65	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6903	Approved
0.6475	Remote Similarity	NPD5281	Approved
0.6475	Remote Similarity	NPD6411	Approved
0.6475	Remote Similarity	NPD7515	Phase 2
0.6475	Remote Similarity	NPD5284	Approved
0.6471	Remote Similarity	NPD7146	Approved
0.6471	Remote Similarity	NPD6684	Approved
0.6471	Remote Similarity	NPD5330	Approved
0.6471	Remote Similarity	NPD6409	Approved
0.6471	Remote Similarity	NPD7521	Approved
0.6471	Remote Similarity	NPD7334	Approved
0.6457	Remote Similarity	NPD5344	Discontinued
0.6457	Remote Similarity	NPD1700	Approved
0.6412	Remote Similarity	NPD5168	Approved
0.641	Remote Similarity	NPD3667	Approved
0.641	Remote Similarity	NPD4223	Phase 3
0.641	Remote Similarity	NPD4221	Approved
0.6393	Remote Similarity	NPD5207	Approved
0.6389	Remote Similarity	NPD7260	Phase 2
0.6387	Remote Similarity	NPD5329	Approved
0.6371	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7900	Approved
0.6357	Remote Similarity	NPD7642	Approved
0.6345	Remote Similarity	NPD8449	Approved
0.6341	Remote Similarity	NPD8035	Phase 2
0.6341	Remote Similarity	NPD8034	Phase 2
0.6333	Remote Similarity	NPD5690	Phase 2
0.632	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6101	Approved
0.6311	Remote Similarity	NPD6904	Approved
0.6311	Remote Similarity	NPD6673	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