NPASS Compound

Structure

CID34837 OpenBabel06191715362D 37 44 0 0 1 0 0 0 0 0999 V2000 -5.9141 5.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 2.6603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9021 0.9515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6499 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7274 1.4273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6497 0.9530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6502 0.9522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0775 1.4282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8251 -0.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2049 4.1572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1227 2.5979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1255 2.3804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7758 3.3327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3798 3.6811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5386 1.4519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3008 3.8097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3800 4.6338 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4839 2.1842 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7281 3.3325 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3005 2.8570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8244 2.3817 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7279 2.3798 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8246 1.4291 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8253 1.4287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9507 2.8566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4755 2.3809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9509 3.8093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8255 2.3813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0007 2.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9032 2.8566 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0002 0.9526 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1259 4.2858 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0780 2.3808 0.0000 N 0 0 0 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 -1.6506 2.8574 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0009 3.8104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 9 1 0 0 0 0 4 6 1 0 0 0 0 4 10 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 8 2 0 0 0 0 7 25 1 0 0 0 0 8 27 1 0 0 0 0 9 34 1 0 0 0 0 10 35 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 21 2 0 0 0 0 13 26 1 0 0 0 0 14 20 1 0 0 0 0 14 28 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 17 33 2 0 0 0 0 18 1 1 1 0 0 0 19 2 1 6 0 0 0 20 11 1 1 0 0 0 20 23 1 0 0 0 0 21 27 1 0 0 0 0 22 12 1 6 0 0 0 22 24 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 1 0 0 0 24 32 1 1 0 0 0 25 29 2 0 0 0 0 25 32 1 0 0 0 0 26 28 2 0 0 0 0 26 31 1 0 0 0 0 27 36 2 0 0 0 0 28 33 1 0 0 0 0 29 30 1 0 0 0 0 29 36 1 0 0 0 0 30 37 2 0 0 0 0 31 15 1 1 0 0 0 31 34 1 0 0 0 0 32 16 1 6 0 0 0 32 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.32
Volume:	527.898
LogP:	4.586
LogD:	3.653
LogS:	-3.457
# Rotatable Bonds:	1
TPSA:	66.91
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.555
Synthetic Accessibility Score:	6.2
Fsp3:	0.656
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.426
MDCK Permeability:	5.728971700591501e-06
Pgp-inhibitor:	0.264
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.766
Plasma Protein Binding (PPB):	67.97917938232422%
Volume Distribution (VD):	2.5
Pgp-substrate:	32.745628356933594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.898
CYP2C19-inhibitor:	0.258
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.259
CYP2D6-inhibitor:	0.129
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.481
CYP3A4-substrate:	0.542

ADMET: Excretion

Clearance (CL):	4.843
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.959
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.423
AMES Toxicity:	0.781
Rat Oral Acute Toxicity:	0.327
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.946
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.858

Download Data

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

Natural Product: NPC34837

Natural Product ID:	NPC34837
*Common Name:**	Complanadine B
IUPAC Name:	n.a.
Synonyms:	Complanadine B
Standard InCHIKey:	RRPXLCVXAVGMCD-PMCZBPHQSA-N
Standard InCHI:	InChI=1S/C32H40N4O/c1-18-11-20-14-28-26(31(15-18)23(20)5-3-9-34-31)13-21(17-33-28)27-8-7-25-29(36-27)30(37)22-12-19(2)16-32(25)24(22)6-4-10-35-32/h7-8,13,17-20,22-24,34-35H,3-6,9-12,14-16H2,1-2H3/t18-,19-,20+,22-,23-,24-,31-,32-/m1/s1
SMILES:	C[C@@H]1C[C@H]2C(=O)c3c([C@@]4(C1)[C@@H]2CCCN4)ccc(n3)c1cnc2c(c1)[C@@]13NCCC[C@@H]3[C@H](C2)C[C@H](C1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644380
PubChem CID:	11488838
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO19825	Litsea japonica	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[14575444]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16309317]
NPO7688	Artemisia selengensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18518	Haematomma nemetzii	Species	Haematommataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19825	Litsea japonica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18499	Podium complanatum	Species	Sphecidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11060	Doris luteorosea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9799	Hebeloma longicaudum	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17577	Azalea ovata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19234	Hymenopappus newberryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19298	Gerbera crocea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17341	Gambeya africana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7688	Artemisia selengensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17887	Penstemon centranthifolius	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19696	Othonna quercifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18023	Vitex quinata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21360	Cordia corymbosa	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19076	Gaillardia pulchella	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19565	Crocus chrysanthus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19869	Fusicolla aquaeductuum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19364	Aconitum chasmanthum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15450	Minuria leptophylla	Species	Asteraceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2624	Individual Protein	Beta-nerve growth factor	Homo sapiens	FC	=	2.3	n.a.	PMID[508319]

☑ 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 NPC34837 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	568
0.1-0.2	3739
0.2-0.3	15213
0.3-0.4	16487
0.4-0.5	3034
0.5-0.6	2379
0.6-0.7	1175
0.7-0.8	96
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.88	High Similarity	NPC201634
0.8708	High Similarity	NPC237188
0.8398	Intermediate Similarity	NPC157583
0.8387	Intermediate Similarity	NPC103119
0.8254	Intermediate Similarity	NPC216550
0.8182	Intermediate Similarity	NPC167635
0.8172	Intermediate Similarity	NPC467063
0.8125	Intermediate Similarity	NPC128244
0.8095	Intermediate Similarity	NPC255909
0.7897	Intermediate Similarity	NPC167710
0.7877	Intermediate Similarity	NPC193740
0.7784	Intermediate Similarity	NPC272458
0.7772	Intermediate Similarity	NPC70949
0.7653	Intermediate Similarity	NPC304203
0.7624	Intermediate Similarity	NPC88115
0.7612	Intermediate Similarity	NPC328596
0.7612	Intermediate Similarity	NPC328318
0.7602	Intermediate Similarity	NPC47190
0.7592	Intermediate Similarity	NPC191415
0.7586	Intermediate Similarity	NPC472065
0.7563	Intermediate Similarity	NPC326422
0.7539	Intermediate Similarity	NPC477042
0.7537	Intermediate Similarity	NPC327592
0.7526	Intermediate Similarity	NPC284775
0.7525	Intermediate Similarity	NPC106757
0.7513	Intermediate Similarity	NPC477003
0.75	Intermediate Similarity	NPC317373
0.75	Intermediate Similarity	NPC472064
0.7464	Intermediate Similarity	NPC237740
0.7452	Intermediate Similarity	NPC318299
0.7446	Intermediate Similarity	NPC80681
0.7438	Intermediate Similarity	NPC472062
0.7438	Intermediate Similarity	NPC472063
0.7438	Intermediate Similarity	NPC472069
0.7416	Intermediate Similarity	NPC317752
0.7402	Intermediate Similarity	NPC317701
0.7374	Intermediate Similarity	NPC476460
0.7326	Intermediate Similarity	NPC265100
0.7308	Intermediate Similarity	NPC473878
0.7302	Intermediate Similarity	NPC216612
0.7291	Intermediate Similarity	NPC284338
0.7282	Intermediate Similarity	NPC102755
0.7269	Intermediate Similarity	NPC322482
0.7268	Intermediate Similarity	NPC70406
0.7264	Intermediate Similarity	NPC157828
0.7264	Intermediate Similarity	NPC195239
0.7259	Intermediate Similarity	NPC118084
0.7258	Intermediate Similarity	NPC56765
0.7258	Intermediate Similarity	NPC474492
0.724	Intermediate Similarity	NPC293216
0.724	Intermediate Similarity	NPC297034
0.7234	Intermediate Similarity	NPC271797
0.7234	Intermediate Similarity	NPC21174
0.7228	Intermediate Similarity	NPC11445
0.7228	Intermediate Similarity	NPC251391
0.7219	Intermediate Similarity	NPC470680
0.7219	Intermediate Similarity	NPC100104
0.7206	Intermediate Similarity	NPC237414
0.7192	Intermediate Similarity	NPC106824
0.7182	Intermediate Similarity	NPC467188
0.715	Intermediate Similarity	NPC324091
0.7143	Intermediate Similarity	NPC472070
0.7135	Intermediate Similarity	NPC262338
0.7121	Intermediate Similarity	NPC308931
0.7121	Intermediate Similarity	NPC133003
0.7121	Intermediate Similarity	NPC99939
0.7105	Intermediate Similarity	NPC42372
0.7104	Intermediate Similarity	NPC105811
0.7098	Intermediate Similarity	NPC252572
0.7081	Intermediate Similarity	NPC470679
0.7081	Intermediate Similarity	NPC217021
0.7074	Intermediate Similarity	NPC41257
0.7074	Intermediate Similarity	NPC318065
0.7074	Intermediate Similarity	NPC206819
0.707	Intermediate Similarity	NPC469727
0.7065	Intermediate Similarity	NPC123906
0.7056	Intermediate Similarity	NPC470677
0.7043	Intermediate Similarity	NPC200743
0.7042	Intermediate Similarity	NPC477413
0.7041	Intermediate Similarity	NPC213468
0.7039	Intermediate Similarity	NPC477004
0.7037	Intermediate Similarity	NPC215584
0.7037	Intermediate Similarity	NPC44773
0.7026	Intermediate Similarity	NPC280852
0.7024	Intermediate Similarity	NPC227582
0.7021	Intermediate Similarity	NPC286427
0.702	Intermediate Similarity	NPC117027
0.7016	Intermediate Similarity	NPC71132
0.7016	Intermediate Similarity	NPC115232
0.701	Intermediate Similarity	NPC477976
0.7005	Intermediate Similarity	NPC252338
0.7005	Intermediate Similarity	NPC73994
0.7	Intermediate Similarity	NPC135601
0.7	Intermediate Similarity	NPC17273
0.7	Intermediate Similarity	NPC141612
0.6995	Remote Similarity	NPC194411
0.6995	Remote Similarity	NPC471386
0.699	Remote Similarity	NPC477041
0.699	Remote Similarity	NPC477044
0.6989	Remote Similarity	NPC470233
0.6986	Remote Similarity	NPC312942
0.6986	Remote Similarity	NPC98715
0.6986	Remote Similarity	NPC327095
0.6983	Remote Similarity	NPC314102
0.6983	Remote Similarity	NPC251722
0.6979	Remote Similarity	NPC56233
0.6976	Remote Similarity	NPC472116
0.6963	Remote Similarity	NPC90723
0.6959	Remote Similarity	NPC473310
0.6957	Remote Similarity	NPC74413
0.6938	Remote Similarity	NPC143977
0.6935	Remote Similarity	NPC471655
0.6935	Remote Similarity	NPC470205
0.6935	Remote Similarity	NPC313889
0.6934	Remote Similarity	NPC116555
0.6931	Remote Similarity	NPC473666
0.6923	Remote Similarity	NPC121327
0.6923	Remote Similarity	NPC469766
0.6919	Remote Similarity	NPC100726
0.6919	Remote Similarity	NPC477974
0.6919	Remote Similarity	NPC182940
0.6919	Remote Similarity	NPC79777
0.6915	Remote Similarity	NPC94752
0.6915	Remote Similarity	NPC209362
0.6912	Remote Similarity	NPC267811
0.6911	Remote Similarity	NPC194881
0.6911	Remote Similarity	NPC242116
0.6908	Remote Similarity	NPC265576
0.6907	Remote Similarity	NPC474897
0.6904	Remote Similarity	NPC83774
0.6895	Remote Similarity	NPC474880
0.6895	Remote Similarity	NPC221786
0.6888	Remote Similarity	NPC139763
0.6888	Remote Similarity	NPC275305
0.6888	Remote Similarity	NPC37423
0.6887	Remote Similarity	NPC225821
0.6887	Remote Similarity	NPC477065
0.6887	Remote Similarity	NPC46225
0.6878	Remote Similarity	NPC51054
0.6875	Remote Similarity	NPC274981
0.6875	Remote Similarity	NPC477045
0.6869	Remote Similarity	NPC215795
0.6869	Remote Similarity	NPC176199
0.6868	Remote Similarity	NPC469784
0.6868	Remote Similarity	NPC469780
0.6868	Remote Similarity	NPC469767
0.6868	Remote Similarity	NPC469761
0.6868	Remote Similarity	NPC469768
0.6868	Remote Similarity	NPC469783
0.6868	Remote Similarity	NPC469779
0.6859	Remote Similarity	NPC229173
0.6857	Remote Similarity	NPC260900
0.6854	Remote Similarity	NPC127677
0.6854	Remote Similarity	NPC258062
0.6853	Remote Similarity	NPC151635
0.6851	Remote Similarity	NPC169433
0.6845	Remote Similarity	NPC24678
0.6845	Remote Similarity	NPC53947
0.6845	Remote Similarity	NPC105818
0.6842	Remote Similarity	NPC213914
0.684	Remote Similarity	NPC142385
0.6837	Remote Similarity	NPC161861
0.6834	Remote Similarity	NPC61011
0.6834	Remote Similarity	NPC471997
0.6834	Remote Similarity	NPC234403
0.6834	Remote Similarity	NPC300688
0.683	Remote Similarity	NPC56109
0.683	Remote Similarity	NPC191382
0.683	Remote Similarity	NPC297862
0.6825	Remote Similarity	NPC211572
0.6825	Remote Similarity	NPC229055
0.6825	Remote Similarity	NPC70922
0.6825	Remote Similarity	NPC212376
0.6825	Remote Similarity	NPC80597
0.6825	Remote Similarity	NPC75540
0.6822	Remote Similarity	NPC271862
0.6818	Remote Similarity	NPC145885
0.6818	Remote Similarity	NPC14113
0.6818	Remote Similarity	NPC84827
0.6818	Remote Similarity	NPC68354
0.6816	Remote Similarity	NPC228835
0.6814	Remote Similarity	NPC268966
0.6814	Remote Similarity	NPC95783
0.6812	Remote Similarity	NPC102592
0.6812	Remote Similarity	NPC79356
0.6811	Remote Similarity	NPC314372
0.6811	Remote Similarity	NPC86288
0.681	Remote Similarity	NPC300183
0.6806	Remote Similarity	NPC470702
0.6806	Remote Similarity	NPC473218
0.6804	Remote Similarity	NPC114637
0.6802	Remote Similarity	NPC40455
0.6796	Remote Similarity	NPC472295
0.6796	Remote Similarity	NPC269886
0.6796	Remote Similarity	NPC81802
0.6796	Remote Similarity	NPC267343
0.6796	Remote Similarity	NPC472210
0.6796	Remote Similarity	NPC247735
0.6794	Remote Similarity	NPC81535
0.6793	Remote Similarity	NPC190296

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 NPC34837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	593
0.2-0.3	1035
0.3-0.4	2158
0.4-0.5	2479
0.5-0.6	1928
0.6-0.7	605
0.7-0.8	50
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8172	Intermediate Similarity	NPD7564	Discontinued
0.8073	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD2481	Approved
0.7725	Intermediate Similarity	NPD2479	Phase 3
0.7696	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5473	Discontinued
0.7624	Intermediate Similarity	NPD7209	Approved
0.7624	Intermediate Similarity	NPD7208	Approved
0.7624	Intermediate Similarity	NPD7207	Approved
0.7622	Intermediate Similarity	NPD6446	Discontinued
0.7609	Intermediate Similarity	NPD3583	Phase 2
0.7526	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD4051	Discontinued
0.7488	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD8115	Approved
0.7451	Intermediate Similarity	NPD8114	Approved
0.7363	Intermediate Similarity	NPD5446	Phase 2
0.7363	Intermediate Similarity	NPD6664	Approved
0.7361	Intermediate Similarity	NPD8289	Discontinued
0.7358	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3323	Discontinued
0.7302	Intermediate Similarity	NPD1343	Approved
0.7273	Intermediate Similarity	NPD7175	Phase 1
0.7268	Intermediate Similarity	NPD7187	Phase 2
0.7264	Intermediate Similarity	NPD7406	Phase 2
0.7245	Intermediate Similarity	NPD6178	Phase 3
0.7219	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7455	Approved
0.7204	Intermediate Similarity	NPD7454	Approved
0.7202	Intermediate Similarity	NPD4075	Phase 2
0.7198	Intermediate Similarity	NPD1270	Approved
0.7194	Intermediate Similarity	NPD7401	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD3394	Approved
0.7183	Intermediate Similarity	NPD3393	Approved
0.7183	Intermediate Similarity	NPD3389	Approved
0.7181	Intermediate Similarity	NPD6771	Discontinued
0.7177	Intermediate Similarity	NPD6459	Phase 2
0.7172	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7204	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7027	Phase 3
0.7136	Intermediate Similarity	NPD4988	Discontinued
0.7136	Intermediate Similarity	NPD3961	Discontinued
0.7128	Intermediate Similarity	NPD3079	Approved
0.7128	Intermediate Similarity	NPD3078	Approved
0.7128	Intermediate Similarity	NPD3077	Approved
0.7128	Intermediate Similarity	NPD3076	Approved
0.7122	Intermediate Similarity	NPD2405	Phase 3
0.7122	Intermediate Similarity	NPD7308	Discontinued
0.7114	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4924	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7191	Phase 2
0.7094	Intermediate Similarity	NPD7619	Phase 3
0.7094	Intermediate Similarity	NPD7618	Phase 3
0.7089	Intermediate Similarity	NPD5888	Phase 2
0.7081	Intermediate Similarity	NPD5491	Phase 3
0.7081	Intermediate Similarity	NPD5489	Phase 1
0.7081	Intermediate Similarity	NPD7010	Phase 3
0.7077	Intermediate Similarity	NPD2753	Discontinued
0.7077	Intermediate Similarity	NPD4181	Approved
0.7075	Intermediate Similarity	NPD6152	Phase 1
0.7059	Intermediate Similarity	NPD4848	Phase 1
0.705	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3238	Discontinued
0.7022	Intermediate Similarity	NPD6986	Phase 1
0.7015	Intermediate Similarity	NPD7234	Approved
0.7015	Intermediate Similarity	NPD7233	Approved
0.7011	Intermediate Similarity	NPD4547	Phase 3
0.7005	Intermediate Similarity	NPD7404	Approved
0.7005	Intermediate Similarity	NPD6479	Discontinued
0.7	Intermediate Similarity	NPD7026	Phase 2
0.7	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5400	Approved
0.6995	Remote Similarity	NPD4922	Phase 2
0.6995	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4883	Approved
0.6971	Remote Similarity	NPD7817	Phase 1
0.6959	Remote Similarity	NPD3610	Approved
0.6959	Remote Similarity	NPD3609	Approved
0.6957	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD2837	Discontinued
0.6948	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3320	Approved
0.6935	Remote Similarity	NPD3318	Approved
0.6935	Remote Similarity	NPD3319	Phase 1
0.6933	Remote Similarity	NPD7789	Approved
0.6933	Remote Similarity	NPD7952	Approved
0.6933	Remote Similarity	NPD7790	Approved
0.6933	Remote Similarity	NPD7953	Approved
0.6933	Remote Similarity	NPD7950	Approved
0.6933	Remote Similarity	NPD7951	Approved
0.6933	Remote Similarity	NPD7791	Approved
0.693	Remote Similarity	NPD8094	Discontinued
0.6923	Remote Similarity	NPD7217	Approved
0.6923	Remote Similarity	NPD7216	Approved
0.6923	Remote Similarity	NPD1722	Approved
0.6919	Remote Similarity	NPD3927	Phase 2
0.6916	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5809	Phase 3
0.6912	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1982	Phase 1
0.6898	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6226	Phase 3
0.6887	Remote Similarity	NPD3905	Phase 3
0.6884	Remote Similarity	NPD2411	Approved
0.6884	Remote Similarity	NPD8093	Discontinued
0.6884	Remote Similarity	NPD4011	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6954	Phase 2
0.6881	Remote Similarity	NPD8431	Approved
0.6881	Remote Similarity	NPD7394	Phase 2
0.6869	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7469	Discontinued
0.6858	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4385	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5853	Phase 3
0.6845	Remote Similarity	NPD5855	Phase 3
0.684	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.684	Remote Similarity	NPD7957	Phase 1
0.683	Remote Similarity	NPD7780	Approved
0.683	Remote Similarity	NPD7781	Approved
0.6825	Remote Similarity	NPD977	Approved
0.6825	Remote Similarity	NPD976	Approved
0.6825	Remote Similarity	NPD975	Approved
0.6823	Remote Similarity	NPD5315	Discontinued
0.6822	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.682	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3506	Approved
0.6818	Remote Similarity	NPD3505	Approved
0.6816	Remote Similarity	NPD3944	Approved
0.6816	Remote Similarity	NPD3942	Approved
0.6814	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1851	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7727	Phase 2
0.6808	Remote Similarity	NPD1506	Discontinued
0.6806	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4128	Approved
0.6791	Remote Similarity	NPD3100	Discontinued
0.6791	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7730	Approved
0.6786	Remote Similarity	NPD7731	Approved
0.6784	Remote Similarity	NPD4076	Approved
0.6784	Remote Similarity	NPD4079	Approved
0.6782	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4298	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2879	Approved
0.6777	Remote Similarity	NPD2881	Approved
0.6776	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7666	Phase 3
0.6776	Remote Similarity	NPD7665	Phase 2
0.6774	Remote Similarity	NPD6787	Phase 2
0.6773	Remote Similarity	NPD5199	Approved
0.6773	Remote Similarity	NPD5198	Approved
0.6769	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6471	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6044	Discontinued
0.6768	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD991	Phase 2
0.6761	Remote Similarity	NPD2119	Approved
0.6761	Remote Similarity	NPD2118	Approved
0.6761	Remote Similarity	NPD992	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5475	Discontinued
0.6758	Remote Similarity	NPD7185	Discontinued
0.6753	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4615	Phase 2
0.6744	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.674	Remote Similarity	NPD1253	Approved
0.674	Remote Similarity	NPD1255	Approved
0.674	Remote Similarity	NPD1256	Approved
0.674	Remote Similarity	NPD1254	Approved
0.6737	Remote Similarity	NPD2165	Phase 1
0.6737	Remote Similarity	NPD2061	Approved
0.6734	Remote Similarity	NPD7111	Discontinued
0.6732	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6470	Phase 3
0.6726	Remote Similarity	NPD7824	Approved
0.6721	Remote Similarity	NPD786	Approved
0.6719	Remote Similarity	NPD3433	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5611	Phase 2
0.6717	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD3799	Suspended
0.6716	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD5426	Phase 3
0.6714	Remote Similarity	NPD5854	Approved
0.6714	Remote Similarity	NPD5901	Discontinued

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