NPASS Compound

Structure

NPC115588 OpenBabel07101718242D 49 58 0 0 1 0 0 0 0 0999 V2000 3.5503 -1.7824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1352 0.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2409 4.1709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8760 4.2592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3552 -0.8017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4646 1.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6601 4.2273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8947 3.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1352 -1.1861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5128 -0.8435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2804 3.7016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7495 3.1530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3698 -0.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9998 0.0299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1005 1.1861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5129 -0.8584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8270 -0.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9811 0.1933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6707 1.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6707 3.0774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 1.6884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2409 0.3577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5118 0.8577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1352 2.9015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3749 1.8577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0971 2.3008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9240 1.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9665 1.8577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9665 2.6709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3698 2.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2409 1.3577 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3749 2.6709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9730 1.3577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8270 2.4741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2848 2.2643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9730 0.3577 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4901 3.2203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4870 0.8734 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1070 -0.1423 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4869 0.8884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1932 1.6065 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1932 2.9221 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 5.9240 0.0487 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 4.1070 1.8577 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.6697 3.0124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8903 4.0204 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2409 3.1709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4829 3.3397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 48 1 0 0 0 0 4 49 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 24 2 0 0 0 0 12 30 2 0 0 0 0 13 39 1 0 0 0 0 14 40 1 0 0 0 0 15 18 1 0 0 0 0 16 43 1 0 0 0 0 17 44 1 0 0 0 0 18 43 1 0 0 0 0 19 25 1 0 0 0 0 19 28 2 0 0 0 0 20 29 2 0 0 0 0 20 32 1 0 0 0 0 21 26 1 0 0 0 0 21 40 1 0 0 0 0 22 31 1 0 0 0 0 22 39 1 0 0 0 0 23 27 1 0 0 0 0 23 44 1 0 0 0 0 24 30 1 0 0 0 0 24 34 1 0 0 0 0 25 32 2 0 0 0 0 26 35 2 0 0 0 0 26 37 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 28 29 1 0 0 0 0 28 41 1 0 0 0 0 29 42 1 0 0 0 0 30 45 1 0 0 0 0 31 25 1 6 0 0 0 31 45 1 0 0 0 0 32 48 1 0 0 0 0 33 36 1 0 0 0 0 33 45 1 0 0 0 0 34 46 2 0 0 0 0 35 41 1 0 0 0 0 35 42 1 0 0 0 0 36 39 1 1 0 0 0 36 44 1 0 0 0 0 37 47 2 0 0 0 0 37 49 1 0 0 0 0 38 40 1 1 0 0 0 38 41 1 0 0 0 0 38 43 1 0 0 0 0 39 5 1 6 0 0 0 40 6 1 6 0 0 0 41 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.34
Volume:	679.638
LogP:	4.349
LogD:	3.289
LogS:	-3.57
# Rotatable Bonds:	6
TPSA:	76.37
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	10
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.234
Synthetic Accessibility Score:	6.006
Fsp3:	0.488
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:	-5.143
MDCK Permeability:	1.8634429579833522e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.902
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.989
Plasma Protein Binding (PPB):	92.79713439941406%
Volume Distribution (VD):	2.769
Pgp-substrate:	6.2910475730896%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.304
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.619
CYP2C9-substrate:	0.502
CYP2D6-inhibitor:	0.846
CYP2D6-substrate:	0.823
CYP3A4-inhibitor:	0.975
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	3.112
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.362
Human Hepatotoxicity (H-HT):	0.776
Drug-inuced Liver Injury (DILI):	0.597
AMES Toxicity:	0.854
Rat Oral Acute Toxicity:	0.862
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.25
Carcinogencity:	0.882
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.406

Download Data

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

Natural Product: NPC115588

Natural Product ID:	NPC115588
*Common Name:**	BCRQAUJZDLCSKQ-CENAIEAJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BCRQAUJZDLCSKQ-CENAIEAJSA-N
Standard InCHI:	InChI=1S/C41H44N4O4/c1-5-39-13-9-17-44-23-27-33(36(39)44)45(30-12-8-7-11-24(30)34(27)46)31(22-39)25-19-28-29(20-32(25)48-3)42-35-26(37(47)49-4)21-40(6-2)14-10-16-43-18-15-41(28,35)38(40)43/h7-14,19-20,31,36,38,42H,5-6,15-18,21-23H2,1-4H3/t31-,36-,38+,39+,40+,41+/m1/s1
SMILES:	COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@](C1)(CC)C=CCN2CC4)cc(c(c3)OC)[C@H]1C[C@]2(CC)C=CCN3[C@@H]2c2n1c1ccccc1c(=O)c2C3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3103571
PubChem CID:	73891100
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002672] Plumeran-type alkaloids

*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
NPO33391	bousigonia angustifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24417634]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	2710.0	nM	PMID[546141]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3610.0	nM	PMID[546141]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7230.0	nM	PMID[546141]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	10550.0	nM	PMID[546141]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	3030.0	nM	PMID[546141]

☑ 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 NPC115588 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	529
0.1-0.2	2653
0.2-0.3	11294
0.3-0.4	7959
0.4-0.5	14678
0.5-0.6	3199
0.6-0.7	1952
0.7-0.8	404
0.8-0.85	24
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9476	High Similarity	NPC151171
0.8492	Intermediate Similarity	NPC22476
0.8235	Intermediate Similarity	NPC303214
0.8213	Intermediate Similarity	NPC232600
0.8095	Intermediate Similarity	NPC87714
0.8095	Intermediate Similarity	NPC475147
0.807	Intermediate Similarity	NPC469722
0.8039	Intermediate Similarity	NPC203628
0.7981	Intermediate Similarity	NPC100863
0.7944	Intermediate Similarity	NPC475133
0.7834	Intermediate Similarity	NPC119722
0.7763	Intermediate Similarity	NPC189661
0.7742	Intermediate Similarity	NPC269449
0.7692	Intermediate Similarity	NPC126556
0.766	Intermediate Similarity	NPC469734
0.7658	Intermediate Similarity	NPC77777
0.7586	Intermediate Similarity	NPC131977
0.756	Intermediate Similarity	NPC5630
0.7555	Intermediate Similarity	NPC223242
0.7534	Intermediate Similarity	NPC195636
0.7532	Intermediate Similarity	NPC469451
0.7521	Intermediate Similarity	NPC469450
0.7511	Intermediate Similarity	NPC127996
0.7489	Intermediate Similarity	NPC139373
0.7478	Intermediate Similarity	NPC128476
0.7468	Intermediate Similarity	NPC154922
0.7468	Intermediate Similarity	NPC329932
0.7458	Intermediate Similarity	NPC469452
0.7437	Intermediate Similarity	NPC475666
0.7437	Intermediate Similarity	NPC293458
0.7434	Intermediate Similarity	NPC476069
0.7407	Intermediate Similarity	NPC67904
0.7395	Intermediate Similarity	NPC81939
0.738	Intermediate Similarity	NPC122886
0.7363	Intermediate Similarity	NPC299582
0.7339	Intermediate Similarity	NPC52801
0.7331	Intermediate Similarity	NPC301501
0.7318	Intermediate Similarity	NPC195787
0.7318	Intermediate Similarity	NPC246140
0.7311	Intermediate Similarity	NPC113455
0.7304	Intermediate Similarity	NPC231924
0.7304	Intermediate Similarity	NPC19175
0.7299	Intermediate Similarity	NPC21425
0.7292	Intermediate Similarity	NPC120239
0.7286	Intermediate Similarity	NPC123241
0.7286	Intermediate Similarity	NPC61013
0.7281	Intermediate Similarity	NPC241263
0.7277	Intermediate Similarity	NPC476220
0.7277	Intermediate Similarity	NPC1820
0.7277	Intermediate Similarity	NPC160113
0.7254	Intermediate Similarity	NPC329982
0.7246	Intermediate Similarity	NPC186669
0.7243	Intermediate Similarity	NPC204970
0.724	Intermediate Similarity	NPC477161
0.7238	Intermediate Similarity	NPC97584
0.7235	Intermediate Similarity	NPC218733
0.7235	Intermediate Similarity	NPC132874
0.7235	Intermediate Similarity	NPC234933
0.7235	Intermediate Similarity	NPC265642
0.7235	Intermediate Similarity	NPC138615
0.7214	Intermediate Similarity	NPC248117
0.7207	Intermediate Similarity	NPC478075
0.7206	Intermediate Similarity	NPC167724
0.7206	Intermediate Similarity	NPC223595
0.7206	Intermediate Similarity	NPC224970
0.7198	Intermediate Similarity	NPC476436
0.7193	Intermediate Similarity	NPC473041
0.7184	Intermediate Similarity	NPC244543
0.7176	Intermediate Similarity	NPC243626
0.7164	Intermediate Similarity	NPC193410
0.7155	Intermediate Similarity	NPC476258
0.7155	Intermediate Similarity	NPC304837
0.715	Intermediate Similarity	NPC474059
0.7126	Intermediate Similarity	NPC478083
0.7119	Intermediate Similarity	NPC476429
0.7117	Intermediate Similarity	NPC313112
0.7117	Intermediate Similarity	NPC301292
0.7115	Intermediate Similarity	NPC203202
0.7115	Intermediate Similarity	NPC264482
0.7104	Intermediate Similarity	NPC473005
0.7097	Intermediate Similarity	NPC230313
0.7093	Intermediate Similarity	NPC473006
0.7087	Intermediate Similarity	NPC288110
0.7082	Intermediate Similarity	NPC237901
0.7082	Intermediate Similarity	NPC195788
0.707	Intermediate Similarity	NPC473569
0.707	Intermediate Similarity	NPC174629
0.7064	Intermediate Similarity	NPC471762
0.7056	Intermediate Similarity	NPC14994
0.7054	Intermediate Similarity	NPC198160
0.7048	Intermediate Similarity	NPC159815
0.7031	Intermediate Similarity	NPC152768
0.7031	Intermediate Similarity	NPC470001
0.7031	Intermediate Similarity	NPC470002
0.7031	Intermediate Similarity	NPC148183
0.7029	Intermediate Similarity	NPC291173
0.7027	Intermediate Similarity	NPC1464
0.7027	Intermediate Similarity	NPC288759
0.7027	Intermediate Similarity	NPC15987
0.7014	Intermediate Similarity	NPC283810
0.7014	Intermediate Similarity	NPC138830
0.7014	Intermediate Similarity	NPC85613
0.7013	Intermediate Similarity	NPC219397
0.7009	Intermediate Similarity	NPC21638
0.7004	Intermediate Similarity	NPC82541
0.7	Intermediate Similarity	NPC169402
0.6992	Remote Similarity	NPC194740
0.6986	Remote Similarity	NPC329338
0.6986	Remote Similarity	NPC469726
0.6982	Remote Similarity	NPC469732
0.6978	Remote Similarity	NPC4687
0.6974	Remote Similarity	NPC116178
0.6973	Remote Similarity	NPC260909
0.6967	Remote Similarity	NPC6974
0.6964	Remote Similarity	NPC268077
0.6963	Remote Similarity	NPC473007
0.696	Remote Similarity	NPC476651
0.696	Remote Similarity	NPC25961
0.6959	Remote Similarity	NPC28510
0.6957	Remote Similarity	NPC234772
0.6948	Remote Similarity	NPC159963
0.6947	Remote Similarity	NPC285192
0.6947	Remote Similarity	NPC205926
0.6943	Remote Similarity	NPC321166
0.6943	Remote Similarity	NPC217903
0.694	Remote Similarity	NPC222046
0.6937	Remote Similarity	NPC127178
0.6934	Remote Similarity	NPC5167
0.6934	Remote Similarity	NPC70092
0.6927	Remote Similarity	NPC99632
0.6927	Remote Similarity	NPC114039
0.6927	Remote Similarity	NPC282339
0.6927	Remote Similarity	NPC206109
0.6927	Remote Similarity	NPC473004
0.692	Remote Similarity	NPC41216
0.692	Remote Similarity	NPC66777
0.6913	Remote Similarity	NPC116238
0.6912	Remote Similarity	NPC473008
0.6911	Remote Similarity	NPC17437
0.691	Remote Similarity	NPC10653
0.691	Remote Similarity	NPC318525
0.6903	Remote Similarity	NPC222561
0.6887	Remote Similarity	NPC218594
0.6887	Remote Similarity	NPC99043
0.6886	Remote Similarity	NPC474366
0.6885	Remote Similarity	NPC473540
0.688	Remote Similarity	NPC46259
0.6878	Remote Similarity	NPC93653
0.6878	Remote Similarity	NPC473458
0.6872	Remote Similarity	NPC330683
0.6872	Remote Similarity	NPC329567
0.6856	Remote Similarity	NPC87413
0.6853	Remote Similarity	NPC305984
0.6844	Remote Similarity	NPC207971
0.684	Remote Similarity	NPC55470
0.684	Remote Similarity	NPC176113
0.6838	Remote Similarity	NPC174760
0.6835	Remote Similarity	NPC313293
0.6831	Remote Similarity	NPC131486
0.6831	Remote Similarity	NPC101350
0.6829	Remote Similarity	NPC36495
0.6828	Remote Similarity	NPC212123
0.6828	Remote Similarity	NPC308943
0.6827	Remote Similarity	NPC214960
0.6827	Remote Similarity	NPC279527
0.6824	Remote Similarity	NPC96321
0.6818	Remote Similarity	NPC471825
0.6818	Remote Similarity	NPC473187
0.6809	Remote Similarity	NPC198503
0.6806	Remote Similarity	NPC52262
0.6805	Remote Similarity	NPC473105
0.6804	Remote Similarity	NPC25401
0.6797	Remote Similarity	NPC30749
0.679	Remote Similarity	NPC235685
0.6781	Remote Similarity	NPC471197
0.6776	Remote Similarity	NPC477066
0.6771	Remote Similarity	NPC23080
0.6771	Remote Similarity	NPC71124
0.6771	Remote Similarity	NPC193906
0.6761	Remote Similarity	NPC127082
0.676	Remote Similarity	NPC67401
0.6754	Remote Similarity	NPC249583
0.6753	Remote Similarity	NPC264176
0.6753	Remote Similarity	NPC310211
0.6753	Remote Similarity	NPC10732
0.6753	Remote Similarity	NPC308137
0.6753	Remote Similarity	NPC305542
0.6752	Remote Similarity	NPC471198
0.6752	Remote Similarity	NPC303658
0.6748	Remote Similarity	NPC478082
0.6748	Remote Similarity	NPC478081
0.6748	Remote Similarity	NPC477067
0.6746	Remote Similarity	NPC303374
0.6743	Remote Similarity	NPC471303
0.6741	Remote Similarity	NPC5374
0.6738	Remote Similarity	NPC330009
0.6737	Remote Similarity	NPC329830
0.6736	Remote Similarity	NPC471513
0.6732	Remote Similarity	NPC100734
0.6732	Remote Similarity	NPC315634

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 NPC115588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	268
0.1-0.2	636
0.2-0.3	809
0.3-0.4	1574
0.4-0.5	2737
0.5-0.6	2182
0.6-0.7	822
0.7-0.8	119
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7324	Intermediate Similarity	NPD5937	Approved
0.7269	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5860	Discontinued
0.7255	Intermediate Similarity	NPD5183	Approved
0.7255	Intermediate Similarity	NPD5186	Approved
0.7252	Intermediate Similarity	NPD4082	Approved
0.7237	Intermediate Similarity	NPD5496	Approved
0.7205	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD3297	Approved
0.72	Intermediate Similarity	NPD4492	Approved
0.72	Intermediate Similarity	NPD4494	Approved
0.7183	Intermediate Similarity	NPD8363	Approved
0.7183	Intermediate Similarity	NPD8364	Approved
0.7175	Intermediate Similarity	NPD4859	Phase 1
0.7149	Intermediate Similarity	NPD3940	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3783	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5433	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD3298	Approved
0.7106	Intermediate Similarity	NPD6199	Discontinued
0.7105	Intermediate Similarity	NPD8149	Discontinued
0.7098	Intermediate Similarity	NPD3472	Approved
0.7098	Intermediate Similarity	NPD4022	Approved
0.7093	Intermediate Similarity	NPD4455	Discontinued
0.7082	Intermediate Similarity	NPD8428	Approved
0.7082	Intermediate Similarity	NPD8427	Approved
0.7082	Intermediate Similarity	NPD8429	Approved
0.7082	Intermediate Similarity	NPD8466	Approved
0.7082	Intermediate Similarity	NPD8467	Approved
0.7082	Intermediate Similarity	NPD8465	Approved
0.708	Intermediate Similarity	NPD4493	Discontinued
0.7054	Intermediate Similarity	NPD4596	Phase 1
0.7048	Intermediate Similarity	NPD3888	Discontinued
0.7035	Intermediate Similarity	NPD3372	Discontinued
0.6996	Remote Similarity	NPD8311	Discontinued
0.6974	Remote Similarity	NPD7225	Discontinued
0.6973	Remote Similarity	NPD8425	Approved
0.6973	Remote Similarity	NPD8459	Approved
0.6973	Remote Similarity	NPD8426	Approved
0.6973	Remote Similarity	NPD8460	Approved
0.6963	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4981	Phase 2
0.6951	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5071	Phase 2
0.6912	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5928	Phase 1
0.6911	Remote Similarity	NPD8358	Approved
0.6907	Remote Similarity	NPD7186	Phase 3
0.69	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD3893	Discontinued
0.6872	Remote Similarity	NPD2907	Approved
0.6872	Remote Similarity	NPD2906	Approved
0.687	Remote Similarity	NPD4356	Discontinued
0.6866	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD6790	Phase 1
0.6828	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4539	Phase 1
0.6803	Remote Similarity	NPD7560	Approved
0.68	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1945	Phase 1
0.6777	Remote Similarity	NPD2248	Approved
0.6777	Remote Similarity	NPD2246	Approved
0.6777	Remote Similarity	NPD5997	Discontinued
0.6776	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3964	Approved
0.6756	Remote Similarity	NPD6238	Discontinued
0.6743	Remote Similarity	NPD4515	Suspended
0.6736	Remote Similarity	NPD6625	Approved
0.6733	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7803	Approved
0.6721	Remote Similarity	NPD4946	Phase 2
0.6714	Remote Similarity	NPD6457	Approved
0.6709	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD4330	Approved
0.6698	Remote Similarity	NPD4329	Approved
0.6695	Remote Similarity	NPD3437	Discontinued
0.6691	Remote Similarity	NPD8489	Phase 1
0.6682	Remote Similarity	NPD3793	Phase 3
0.6681	Remote Similarity	NPD6321	Discontinued
0.6681	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.668	Remote Similarity	NPD4952	Phase 3
0.6667	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7955	Approved
0.6667	Remote Similarity	NPD7922	Phase 1
0.6667	Remote Similarity	NPD6874	Approved
0.6667	Remote Similarity	NPD6644	Discontinued
0.6667	Remote Similarity	NPD7956	Approved
0.6652	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8027	Approved
0.6652	Remote Similarity	NPD5504	Discontinued
0.6651	Remote Similarity	NPD7479	Phase 2
0.6651	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD3289	Phase 3
0.6637	Remote Similarity	NPD3290	Approved
0.6636	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4668	Phase 2
0.662	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5445	Approved
0.6611	Remote Similarity	NPD3912	Discontinued
0.6605	Remote Similarity	NPD3792	Approved
0.6605	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5488	Discontinued
0.6598	Remote Similarity	NPD4373	Phase 2
0.6598	Remote Similarity	NPD7994	Phase 2
0.6591	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7627	Approved
0.6579	Remote Similarity	NPD7626	Approved
0.6578	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD7708	Approved
0.6568	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD683	Approved
0.6553	Remote Similarity	NPD7559	Phase 2
0.6552	Remote Similarity	NPD7925	Phase 2
0.6552	Remote Similarity	NPD7924	Phase 2
0.655	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7279	Phase 2
0.6542	Remote Similarity	NPD7278	Phase 2
0.6529	Remote Similarity	NPD3259	Approved
0.6528	Remote Similarity	NPD5600	Discontinued
0.6525	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4467	Phase 2
0.6522	Remote Similarity	NPD4465	Phase 2
0.6522	Remote Similarity	NPD6250	Discontinued
0.6507	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD3828	Approved
0.6498	Remote Similarity	NPD8461	Discontinued
0.6498	Remote Similarity	NPD8091	Phase 3
0.6496	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD2681	Approved
0.6479	Remote Similarity	NPD2037	Approved
0.6479	Remote Similarity	NPD2680	Approved
0.6478	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7570	Approved
0.6473	Remote Similarity	NPD7569	Approved
0.6471	Remote Similarity	NPD5632	Approved
0.6466	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.646	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5482	Discontinued
0.6452	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3965	Phase 1
0.645	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7528	Approved
0.6438	Remote Similarity	NPD3470	Approved
0.6438	Remote Similarity	NPD3471	Approved
0.6435	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5515	Phase 2
0.6425	Remote Similarity	NPD6618	Phase 2
0.6423	Remote Similarity	NPD4885	Approved
0.6422	Remote Similarity	NPD3782	Discontinued
0.6419	Remote Similarity	NPD2431	Approved
0.6419	Remote Similarity	NPD2432	Approved
0.6415	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3874	Discontinued
0.6409	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD8281	Discontinued
0.6407	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5197	Approved
0.6404	Remote Similarity	NPD5196	Approved
0.6404	Remote Similarity	NPD5194	Approved
0.6402	Remote Similarity	NPD2454	Approved
0.6402	Remote Similarity	NPD2455	Approved
0.64	Remote Similarity	NPD4302	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD6357	Discontinued
0.639	Remote Similarity	NPD7598	Phase 2
0.639	Remote Similarity	NPD1802	Approved
0.639	Remote Similarity	NPD1801	Approved
0.6389	Remote Similarity	NPD3377	Discontinued
0.6387	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4368	Phase 2
0.6368	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.636	Remote Similarity	NPD5195	Discontinued
0.6359	Remote Similarity	NPD3422	Phase 3
0.6359	Remote Similarity	NPD3423	Phase 2
0.6356	Remote Similarity	NPD7272	Discontinued
0.6345	Remote Similarity	NPD7853	Phase 2
0.6343	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD955	Approved
0.6336	Remote Similarity	NPD7205	Discontinued
0.6335	Remote Similarity	NPD8016	Phase 3
0.6335	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD3983	Phase 3
0.6326	Remote Similarity	NPD3984	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