NPASS Compound

Structure

NPC329932 OpenBabel07101718192D 55 67 0 0 1 0 0 0 0 0999 V2000 -0.9889 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6261 3.7879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4997 -2.8677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4133 -2.4609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6907 -2.2799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5178 -1.4664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2320 -2.7250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4351 -1.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0662 -0.3410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6139 1.1368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6143 -2.2150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7168 -0.8287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6261 -2.0811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8369 1.3765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2599 -3.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3720 -2.3186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1756 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5932 -2.4996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1261 1.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5950 -2.7440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6408 -3.1351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1261 1.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7952 -1.2854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7088 -0.8786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6261 0.3238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6261 2.0558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1261 -0.5422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6409 -1.5860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8566 0.0610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0098 -1.3962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6261 0.3238 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1829 -2.2579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5823 -0.7045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1261 -0.5422 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6042 0.1159 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.4540 -1.5982 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -2.8171 -1.4933 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1221 -3.7817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6261 2.0558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4714 -2.2389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 2.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1261 2.9219 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3689 0.7116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 53 1 0 0 0 0 2 54 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 2 0 0 0 0 5 9 1 0 0 0 0 6 28 2 0 0 0 0 7 29 1 0 0 0 0 8 30 2 0 0 0 0 9 31 2 0 0 0 0 10 14 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 43 1 0 0 0 0 13 17 1 0 0 0 0 14 46 1 0 0 0 0 15 46 1 0 0 0 0 16 47 1 0 0 0 0 17 55 1 0 0 0 0 18 24 1 0 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 21 40 1 0 0 0 0 22 27 1 0 0 0 0 22 39 1 0 0 0 0 23 41 1 0 0 0 0 23 48 1 0 0 0 0 24 40 1 6 0 0 0 25 44 1 1 0 0 0 26 49 2 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 28 30 1 0 0 0 0 28 42 1 0 0 0 0 29 32 2 0 0 0 0 29 43 1 0 0 0 0 30 45 1 0 0 0 0 31 32 1 0 0 0 0 31 53 1 0 0 0 0 32 48 1 0 0 0 0 33 42 1 0 0 0 0 33 45 1 0 0 0 0 34 50 2 0 0 0 0 34 54 1 0 0 0 0 35 39 1 6 0 0 0 35 42 1 0 0 0 0 35 47 1 0 0 0 0 36 40 1 1 0 0 0 36 43 1 0 0 0 0 36 46 1 0 0 0 0 37 39 1 1 0 0 0 37 41 1 0 0 0 0 37 55 1 0 0 0 0 38 41 1 1 0 0 0 38 47 1 0 0 0 0 38 51 1 0 0 0 0 39 13 1 1 0 0 0 40 19 1 1 0 0 0 41 20 1 1 0 0 0 42 11 1 6 0 0 0 43 44 1 1 0 0 0 44 48 1 0 0 0 0 44 52 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	746.37
Volume:	740.136
LogP:	2.759
LogD:	2.45
LogS:	-4.38
# Rotatable Bonds:	3
TPSA:	124.37
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	13
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	7.341
Fsp3:	0.659
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:	-5.616
MDCK Permeability:	1.3484213013725821e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.243
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.515
Plasma Protein Binding (PPB):	56.781517028808594%
Volume Distribution (VD):	1.807
Pgp-substrate:	37.36697006225586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.563
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.782
CYP2D6-substrate:	0.845
CYP3A4-inhibitor:	0.944
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	4.522
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.965
Human Hepatotoxicity (H-HT):	0.823
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.392
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.044
Carcinogencity:	0.924
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC329932

Natural Product ID:	NPC329932
*Common Name:**	Biscarpamontamine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SCPIROZFVJWUFE-LLSOSBHTSA-N
Standard InCHI:	InChI=1S/C44H50N4O7/c1-53-31-9-5-7-29-32(31)48-23-41(20-25-19-40-21-26(49)18-24(40)10-14-46-15-12-43(29,36(40)46)44(25,48)52)37-39(13-17-55-37)22-27(34(50)54-2)33-42(11-16-47(35(39)42)38(41)51)28-6-3-4-8-30(28)45-33/h3-9,24-25,35-38,45,51-52H,10-23H2,1-2H3/t24-,25+,35+,36+,37-,38-,39+,40+,41+,42+,43-,44-/m1/s1
SMILES:	COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@@]5(C1)CCO[C@H]5[C@]1([C@H](N2CC4)O)C[C@@H]2C[C@]45CC(=O)C[C@H]4CCN4[C@@H]5[C@@]5([C@]2(N(C1)c1c(OC)cccc51)O)CC4)cccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079127
PubChem CID:	46883150
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002755] Aspidospermatan-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
NPO33497	tabernaemontana sphaerocarpa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19711971]

☑ 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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	500.0	nM	PMID[518170]
NPT389	Cell Line	RPMI-8226	Homo sapiens	IC50	=	1900.0	nM	PMID[518170]
NPT405	Cell Line	NCI-H226	Homo sapiens	IC50	=	2400.0	nM	PMID[518170]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	800.0	nM	PMID[518170]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1800.0	nM	PMID[518170]

☑ 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 NPC329932 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	392
0.1-0.2	1740
0.2-0.3	4593
0.3-0.4	12239
0.4-0.5	16712
0.5-0.6	6153
0.6-0.7	721
0.7-0.8	114
0.8-0.85	16
0.85-0.9	4
0.9-0.95	5
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC469452
0.9907	High Similarity	NPC469451
0.9814	High Similarity	NPC469450
0.9676	High Similarity	NPC301501
0.9539	High Similarity	NPC131977
0.9444	High Similarity	NPC139373
0.9442	High Similarity	NPC223242
0.869	High Similarity	NPC469722
0.838	Intermediate Similarity	NPC246140
0.838	Intermediate Similarity	NPC195787
0.8	Intermediate Similarity	NPC87714
0.7991	Intermediate Similarity	NPC1464
0.7932	Intermediate Similarity	NPC151171
0.7885	Intermediate Similarity	NPC234772
0.787	Intermediate Similarity	NPC128476
0.7851	Intermediate Similarity	NPC195636
0.7848	Intermediate Similarity	NPC154922
0.7845	Intermediate Similarity	NPC19175
0.7841	Intermediate Similarity	NPC189661
0.7817	Intermediate Similarity	NPC77777
0.7778	Intermediate Similarity	NPC471513
0.7749	Intermediate Similarity	NPC476069
0.7702	Intermediate Similarity	NPC473458
0.7686	Intermediate Similarity	NPC113455
0.7664	Intermediate Similarity	NPC120239
0.7657	Intermediate Similarity	NPC160113
0.7657	Intermediate Similarity	NPC476220
0.7617	Intermediate Similarity	NPC231924
0.7568	Intermediate Similarity	NPC138615
0.7568	Intermediate Similarity	NPC132874
0.7568	Intermediate Similarity	NPC218733
0.7568	Intermediate Similarity	NPC265642
0.7563	Intermediate Similarity	NPC477397
0.7554	Intermediate Similarity	NPC288110
0.7552	Intermediate Similarity	NPC291173
0.755	Intermediate Similarity	NPC329982
0.7531	Intermediate Similarity	NPC476258
0.7531	Intermediate Similarity	NPC304837
0.748	Intermediate Similarity	NPC477393
0.7479	Intermediate Similarity	NPC222046
0.7468	Intermediate Similarity	NPC115588
0.7455	Intermediate Similarity	NPC22476
0.7446	Intermediate Similarity	NPC127996
0.7437	Intermediate Similarity	NPC476436
0.7435	Intermediate Similarity	NPC269449
0.7419	Intermediate Similarity	NPC477396
0.7398	Intermediate Similarity	NPC477395
0.7397	Intermediate Similarity	NPC14994
0.7389	Intermediate Similarity	NPC232600
0.738	Intermediate Similarity	NPC478075
0.7376	Intermediate Similarity	NPC25401
0.7373	Intermediate Similarity	NPC159963
0.7371	Intermediate Similarity	NPC119722
0.7368	Intermediate Similarity	NPC475147
0.7355	Intermediate Similarity	NPC476429
0.7339	Intermediate Similarity	NPC97584
0.733	Intermediate Similarity	NPC5630
0.7316	Intermediate Similarity	NPC475133
0.7315	Intermediate Similarity	NPC99043
0.7315	Intermediate Similarity	NPC218594
0.73	Intermediate Similarity	NPC10653
0.73	Intermediate Similarity	NPC318525
0.7297	Intermediate Similarity	NPC203628
0.7244	Intermediate Similarity	NPC303214
0.7222	Intermediate Similarity	NPC203202
0.7222	Intermediate Similarity	NPC264482
0.7212	Intermediate Similarity	NPC90967
0.7193	Intermediate Similarity	NPC138830
0.7189	Intermediate Similarity	NPC186669
0.7181	Intermediate Similarity	NPC100863
0.7178	Intermediate Similarity	NPC477394
0.7173	Intermediate Similarity	NPC126556
0.7162	Intermediate Similarity	NPC469732
0.7162	Intermediate Similarity	NPC21425
0.7118	Intermediate Similarity	NPC67904
0.7107	Intermediate Similarity	NPC122886
0.7103	Intermediate Similarity	NPC469734
0.7098	Intermediate Similarity	NPC474059
0.7094	Intermediate Similarity	NPC477160
0.7094	Intermediate Similarity	NPC471303
0.708	Intermediate Similarity	NPC470485
0.7078	Intermediate Similarity	NPC6974
0.7069	Intermediate Similarity	NPC470484
0.7069	Intermediate Similarity	NPC329833
0.7041	Intermediate Similarity	NPC237901
0.7041	Intermediate Similarity	NPC195788
0.7009	Intermediate Similarity	NPC181928
0.7004	Intermediate Similarity	NPC475720
0.7004	Intermediate Similarity	NPC475316
0.7004	Intermediate Similarity	NPC473486
0.7004	Intermediate Similarity	NPC159815
0.7004	Intermediate Similarity	NPC474192
0.6991	Remote Similarity	NPC470483
0.6983	Remote Similarity	NPC473005
0.6977	Remote Similarity	NPC478080
0.6976	Remote Similarity	NPC473105
0.6975	Remote Similarity	NPC473006
0.6964	Remote Similarity	NPC35390
0.6964	Remote Similarity	NPC470631
0.6964	Remote Similarity	NPC473781
0.6947	Remote Similarity	NPC22689
0.6947	Remote Similarity	NPC105055
0.6937	Remote Similarity	NPC260909
0.692	Remote Similarity	NPC52262
0.6913	Remote Similarity	NPC162440
0.691	Remote Similarity	NPC474077
0.6905	Remote Similarity	NPC475816
0.6901	Remote Similarity	NPC219397
0.6901	Remote Similarity	NPC223590
0.69	Remote Similarity	NPC34717
0.6888	Remote Similarity	NPC473837
0.6885	Remote Similarity	NPC478083
0.6867	Remote Similarity	NPC471512
0.6863	Remote Similarity	NPC81939
0.6842	Remote Similarity	NPC248903
0.6836	Remote Similarity	NPC475666
0.6826	Remote Similarity	NPC243626
0.6826	Remote Similarity	NPC230313
0.6824	Remote Similarity	NPC475489
0.6822	Remote Similarity	NPC476500
0.6822	Remote Similarity	NPC477161
0.6809	Remote Similarity	NPC17437
0.6802	Remote Similarity	NPC26928
0.6798	Remote Similarity	NPC473298
0.6778	Remote Similarity	NPC474366
0.677	Remote Similarity	NPC476095
0.6768	Remote Similarity	NPC284685
0.6767	Remote Similarity	NPC88923
0.6767	Remote Similarity	NPC100734
0.6767	Remote Similarity	NPC315634
0.6763	Remote Similarity	NPC30749
0.6762	Remote Similarity	NPC475609
0.6761	Remote Similarity	NPC21638
0.6759	Remote Similarity	NPC248117
0.6758	Remote Similarity	NPC167724
0.6758	Remote Similarity	NPC223595
0.6758	Remote Similarity	NPC224970
0.6748	Remote Similarity	NPC148124
0.6748	Remote Similarity	NPC251071
0.6744	Remote Similarity	NPC61013
0.6742	Remote Similarity	NPC191489
0.6735	Remote Similarity	NPC472099
0.6723	Remote Similarity	NPC212123
0.6723	Remote Similarity	NPC198160
0.6722	Remote Similarity	NPC470482
0.6722	Remote Similarity	NPC470481
0.6721	Remote Similarity	NPC473667
0.6719	Remote Similarity	NPC477067
0.6719	Remote Similarity	NPC478082
0.6713	Remote Similarity	NPC193410
0.6711	Remote Similarity	NPC285841
0.6708	Remote Similarity	NPC25961
0.6707	Remote Similarity	NPC46259
0.6707	Remote Similarity	NPC99724
0.6696	Remote Similarity	NPC473007
0.6695	Remote Similarity	NPC330683
0.6695	Remote Similarity	NPC329567
0.6695	Remote Similarity	NPC161804
0.6694	Remote Similarity	NPC217903
0.6681	Remote Similarity	NPC127178
0.6681	Remote Similarity	NPC221687
0.668	Remote Similarity	NPC250960
0.668	Remote Similarity	NPC74216
0.668	Remote Similarity	NPC71539
0.668	Remote Similarity	NPC477066
0.6667	Remote Similarity	NPC266994
0.6667	Remote Similarity	NPC176113
0.6667	Remote Similarity	NPC473004
0.6667	Remote Similarity	NPC473880
0.6667	Remote Similarity	NPC140311
0.6654	Remote Similarity	NPC478081
0.6654	Remote Similarity	NPC473540
0.6653	Remote Similarity	NPC10732
0.6653	Remote Similarity	NPC116178
0.6653	Remote Similarity	NPC305542
0.6652	Remote Similarity	NPC473008
0.6651	Remote Similarity	NPC293458
0.664	Remote Similarity	NPC470480
0.6636	Remote Similarity	NPC36495
0.6626	Remote Similarity	NPC321166
0.6625	Remote Similarity	NPC94687
0.6625	Remote Similarity	NPC476495
0.6625	Remote Similarity	NPC471950
0.6625	Remote Similarity	NPC106840
0.6625	Remote Similarity	NPC471945
0.6624	Remote Similarity	NPC475223
0.6624	Remote Similarity	NPC52801
0.6624	Remote Similarity	NPC472191
0.6623	Remote Similarity	NPC28510
0.6613	Remote Similarity	NPC106593
0.6612	Remote Similarity	NPC82541
0.6612	Remote Similarity	NPC218303
0.6609	Remote Similarity	NPC217294
0.6609	Remote Similarity	NPC230098
0.6598	Remote Similarity	NPC471951
0.6598	Remote Similarity	NPC476496
0.6598	Remote Similarity	NPC471946
0.6597	Remote Similarity	NPC207971
0.6597	Remote Similarity	NPC475448
0.6597	Remote Similarity	NPC246983

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 NPC329932 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	630
0.2-0.3	883
0.3-0.4	2265
0.4-0.5	3237
0.5-0.6	1731
0.6-0.7	180
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7137	Intermediate Similarity	NPD8364	Approved
0.7137	Intermediate Similarity	NPD8363	Approved
0.7083	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8467	Approved
0.7041	Intermediate Similarity	NPD8466	Approved
0.7041	Intermediate Similarity	NPD8465	Approved
0.6942	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8459	Approved
0.6937	Remote Similarity	NPD8426	Approved
0.6937	Remote Similarity	NPD8460	Approved
0.6937	Remote Similarity	NPD8425	Approved
0.6914	Remote Similarity	NPD8428	Approved
0.6914	Remote Similarity	NPD8429	Approved
0.6914	Remote Similarity	NPD8427	Approved
0.6908	Remote Similarity	NPD6625	Approved
0.688	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6199	Discontinued
0.6851	Remote Similarity	NPD6644	Discontinued
0.6835	Remote Similarity	NPD4082	Approved
0.682	Remote Similarity	NPD4493	Discontinued
0.6818	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD8358	Approved
0.6792	Remote Similarity	NPD4494	Approved
0.6792	Remote Similarity	NPD4492	Approved
0.6778	Remote Similarity	NPD5860	Discontinued
0.6768	Remote Similarity	NPD7955	Approved
0.6768	Remote Similarity	NPD7956	Approved
0.6767	Remote Similarity	NPD7803	Approved
0.6742	Remote Similarity	NPD7708	Approved
0.6735	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8461	Discontinued
0.6723	Remote Similarity	NPD4596	Phase 1
0.6709	Remote Similarity	NPD6874	Approved
0.6695	Remote Similarity	NPD2906	Approved
0.6695	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD2907	Approved
0.6667	Remote Similarity	NPD3437	Discontinued
0.6667	Remote Similarity	NPD8489	Phase 1
0.6652	Remote Similarity	NPD5928	Phase 1
0.664	Remote Similarity	NPD6723	Discontinued
0.6639	Remote Similarity	NPD3893	Discontinued
0.6637	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4455	Discontinued
0.6625	Remote Similarity	NPD3472	Approved
0.6625	Remote Similarity	NPD4022	Approved
0.6612	Remote Similarity	NPD1945	Phase 1
0.6609	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7186	Phase 3
0.6593	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3006	Discontinued
0.6586	Remote Similarity	NPD7278	Phase 2
0.6586	Remote Similarity	NPD3912	Discontinued
0.6586	Remote Similarity	NPD7279	Phase 2
0.6584	Remote Similarity	NPD3888	Discontinued
0.6584	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6238	Discontinued
0.6571	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3372	Discontinued
0.6569	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4846	Phase 2
0.656	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4859	Phase 1
0.6555	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7497	Discontinued
0.652	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.652	Remote Similarity	NPD7820	Phase 3
0.6518	Remote Similarity	NPD7293	Approved
0.6513	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7476	Discontinued
0.6511	Remote Similarity	NPD5582	Discontinued
0.6509	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD5186	Approved
0.6502	Remote Similarity	NPD5183	Approved
0.65	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD5496	Approved
0.6483	Remote Similarity	NPD2974	Approved
0.6483	Remote Similarity	NPD2973	Approved
0.6483	Remote Similarity	NPD2975	Approved
0.6483	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6997	Phase 2
0.6476	Remote Similarity	NPD7479	Phase 2
0.6475	Remote Similarity	NPD5676	Approved
0.6473	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4580	Approved
0.6468	Remote Similarity	NPD7256	Discontinued
0.6463	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6716	Phase 1
0.6456	Remote Similarity	NPD5071	Phase 2
0.6449	Remote Similarity	NPD7827	Phase 1
0.6448	Remote Similarity	NPD7560	Approved
0.6447	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD8149	Discontinued
0.6432	Remote Similarity	NPD4465	Phase 2
0.6432	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD4467	Phase 2
0.6426	Remote Similarity	NPD2899	Discontinued
0.642	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7925	Phase 2
0.641	Remote Similarity	NPD7924	Phase 2
0.6405	Remote Similarity	NPD6905	Phase 2
0.6404	Remote Similarity	NPD8492	Approved
0.6392	Remote Similarity	NPD4981	Phase 2
0.6389	Remote Similarity	NPD7542	Phase 3
0.6387	Remote Similarity	NPD4668	Phase 2
0.6387	Remote Similarity	NPD4420	Approved
0.6384	Remote Similarity	NPD2247	Approved
0.6384	Remote Similarity	NPD2249	Approved
0.6384	Remote Similarity	NPD2681	Approved
0.6384	Remote Similarity	NPD2680	Approved
0.6381	Remote Similarity	NPD7922	Phase 1
0.6378	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2494	Approved
0.6375	Remote Similarity	NPD3452	Approved
0.6375	Remote Similarity	NPD7805	Phase 3
0.6375	Remote Similarity	NPD3450	Approved
0.6375	Remote Similarity	NPD2493	Approved
0.6375	Remote Similarity	NPD6321	Discontinued
0.6371	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6367	Remote Similarity	NPD8463	Approved
0.6364	Remote Similarity	NPD4583	Approved
0.6364	Remote Similarity	NPD4040	Phase 1
0.6364	Remote Similarity	NPD7891	Discontinued
0.6364	Remote Similarity	NPD1769	Discontinued
0.6364	Remote Similarity	NPD4582	Approved
0.636	Remote Similarity	NPD7810	Phase 3
0.636	Remote Similarity	NPD7811	Phase 3
0.6356	Remote Similarity	NPD5610	Approved
0.6349	Remote Similarity	NPD5005	Approved
0.6349	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD5006	Approved
0.6344	Remote Similarity	NPD5938	Phase 3
0.634	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4004	Approved
0.6322	Remote Similarity	NPD4002	Approved
0.6311	Remote Similarity	NPD7126	Discontinued
0.6311	Remote Similarity	NPD6457	Approved
0.631	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD2968	Approved
0.6293	Remote Similarity	NPD2971	Approved
0.6292	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5600	Discontinued
0.6288	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7262	Phase 1
0.6282	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7272	Discontinued
0.6271	Remote Similarity	NPD2490	Approved
0.6271	Remote Similarity	NPD2488	Approved
0.627	Remote Similarity	NPD8161	Suspended
0.6266	Remote Similarity	NPD6851	Approved
0.6266	Remote Similarity	NPD6853	Approved
0.6266	Remote Similarity	NPD4107	Approved
0.6264	Remote Similarity	NPD8359	Phase 2
0.6255	Remote Similarity	NPD8367	Approved
0.6255	Remote Similarity	NPD8025	Phase 2
0.6255	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD7048	Phase 3
0.6245	Remote Similarity	NPD2434	Approved
0.6245	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD7556	Discontinued
0.6239	Remote Similarity	NPD3983	Phase 3
0.6239	Remote Similarity	NPD6107	Approved
0.6239	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD7432	Phase 2
0.6236	Remote Similarity	NPD7417	Discontinued
0.6234	Remote Similarity	NPD3964	Approved
0.623	Remote Similarity	NPD1294	Discontinued
0.6229	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8027	Approved
0.622	Remote Similarity	NPD2514	Approved
0.6216	Remote Similarity	NPD7797	Approved
0.6216	Remote Similarity	NPD7796	Approved
0.6214	Remote Similarity	NPD3057	Approved
0.6213	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD8255	Phase 2
0.6198	Remote Similarity	NPD8016	Phase 3
0.6198	Remote Similarity	NPD6519	Phase 2
0.6198	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD8152	Approved
0.6194	Remote Similarity	NPD8153	Approved
0.6194	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD4373	Phase 2
0.619	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6189	Remote Similarity	NPD4946	Phase 2
0.6188	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD7301	Phase 3
0.6183	Remote Similarity	NPD5196	Approved
0.6183	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5197	Approved
0.6183	Remote Similarity	NPD5194	Approved
0.6181	Remote Similarity	NPD7907	Approved
0.6181	Remote Similarity	NPD8155	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