NPASS Compound

Structure

CID195457 OpenBabel06191715582D 40 45 0 0 1 0 0 0 0 0999 V2000 4.4961 0.3173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1200 -3.3044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4474 1.7586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4279 -2.2870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9562 3.1954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6176 -1.2676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8090 0.2266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8964 -2.6485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5510 2.7411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4694 3.4294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3395 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8289 1.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4994 -0.6685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0011 -1.3392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9890 1.1611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8303 -1.8286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6685 2.4994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1594 -0.6699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1685 0.4916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1611 -2.0082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0009 2.3195 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6699 1.1594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2159 1.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8302 -1.0555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0555 1.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3863 -0.6697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4992 0.1046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7741 -1.3390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6741 0.5790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0247 3.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3390 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0007 1.5464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6697 0.3863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8295 0.4908 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1604 -0.6692 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6691 1.1601 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 -2.4358 0.5786 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9430 4.5326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6616 3.5708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 8 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 10 30 1 0 0 0 0 11 22 1 0 0 0 0 11 29 1 0 0 0 0 12 23 2 0 0 0 0 12 25 1 0 0 0 0 13 24 1 0 0 0 0 13 27 2 0 0 0 0 14 26 1 0 0 0 0 14 28 2 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 24 1 0 0 0 0 17 5 1 6 0 0 0 17 21 1 0 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 18 31 1 0 0 0 0 19 27 1 0 0 0 0 20 28 1 0 0 0 0 21 9 1 1 0 0 0 21 32 1 0 0 0 0 22 32 2 0 0 0 0 22 33 1 0 0 0 0 23 34 1 0 0 0 0 24 35 2 0 0 0 0 25 36 2 0 0 0 0 26 37 1 0 0 0 0 27 34 1 0 0 0 0 28 35 1 0 0 0 0 29 31 1 0 0 0 0 29 38 2 0 0 0 0 30 39 2 0 0 0 0 30 40 1 0 0 0 0 31 33 2 0 0 0 0 32 36 1 0 0 0 0 33 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.26
Volume:	564.069
LogP:	6.317
LogD:	4.288
LogS:	-5.131
# Rotatable Bonds:	4
TPSA:	117.53
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.277
Synthetic Accessibility Score:	6.513
Fsp3:	0.273
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.87
MDCK Permeability:	3.772698164539179e-06
Pgp-inhibitor:	0.021
Pgp-substrate:	0.949
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.877
30% Bioavailability (F30%):	0.826

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	100.40531158447266%
Volume Distribution (VD):	0.091
Pgp-substrate:	2.105429172515869%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.198
CYP2C19-substrate:	0.091
CYP2C9-inhibitor:	0.861
CYP2C9-substrate:	0.925
CYP2D6-inhibitor:	0.378
CYP2D6-substrate:	0.853
CYP3A4-inhibitor:	0.644
CYP3A4-substrate:	0.88

ADMET: Excretion

Clearance (CL):	1.921
Half-life (T1/2):	0.7

ADMET: Toxicity

hERG Blockers:	0.903
Human Hepatotoxicity (H-HT):	0.943
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.455
Rat Oral Acute Toxicity:	0.997
Maximum Recommended Daily Dose:	0.96
Skin Sensitization:	0.242
Carcinogencity:	0.93
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.991

Download Data

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

Natural Product: NPC195457

Natural Product ID:	NPC195457
*Common Name:**	Pyropheophorbide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IEGUQQKIFBYXLG-CDIXLCFRSA-N
Standard InCHI:	InChI=1S/C33H34N4O3/c1-7-19-15(3)23-12-25-17(5)21(9-10-30(39)40)32(36-25)22-11-29(38)31-18(6)26(37-33(22)31)14-28-20(8-2)16(4)24(35-28)13-27(19)34-23/h7,12-14,17,21,34,37H,1,8-11H2,2-6H3,(H,39,40)/b23-12-,24-13-,25-12-,26-14-,27-13-,28-14-,32-22-/t17-,21-/m0/s1
SMILES:	C=Cc1c(C)/c/2=C/C3=N/C(=C4/CC(=O)c5c(C)c(C=C6/C(=C(C)/C(=N6)C=c1/[nH]2)CC)[nH]c45)/[C@@H](CCC(=O)O)[C@@H]3C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520220
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568778]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	Uzbekistan	n.a.	PMID[15568778]
NPO11171	Stelletta clavosa	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21280591]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21955940]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27280968]
NPO18739	Exallage chrysotricha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6855	Chaenostoma foetidum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7014	Retaster insignis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12904	Nauclea coadunata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18739	Exallage chrysotricha	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9400	Mutisia homoeantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11025	Cryptocarya leucophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14193	Pleiococca wilcoxiana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11879	Polistes rothneyi	Species	Vespidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1444	Thalictrum amurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6693	Streptomyces triangulatus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16259	Syringa reticulata	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25737	Solanum pimpinellifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13207	Leptoclinides durus	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11171	Stelletta clavosa	Species	Ancorinidae	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	13

Activity Type	# Activity
Individual Protein	1
Organism	7
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2620	Individual Protein	Seed linoleate 9S-lipoxygenase	Glycine max	Inhibition	=	15.0	%	PMID[546026]
NPT35	Others	n.a.		K	=	5.78	10'2/min	PMID[546027]
NPT35	Others	n.a.		LogP	=	3.77	n.a.	PMID[546028]
NPT35	Others	n.a.		Ratio	=	0.405	n.a.	PMID[546028]
NPT35	Others	n.a.		Activity	=	661.0	nm	PMID[546028]
NPT35	Others	n.a.		K	=	0.0081	/s	PMID[546028]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	13.1	mg	PMID[546028]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	12.7	mg	PMID[546028]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	13.2	mg	PMID[546028]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	13.3	mg	PMID[546028]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Activity	=	57.2	mg	PMID[546028]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Activity	=	59.2	mg	PMID[546028]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Activity	=	100.3	mg	PMID[546028]

☑ 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 NPC195457 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	305
0.1-0.2	2032
0.2-0.3	12339
0.3-0.4	20201
0.4-0.5	3875
0.5-0.6	2475
0.6-0.7	1320
0.7-0.8	141
0.8-0.85	1
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9409	High Similarity	NPC187255
0.9247	High Similarity	NPC257175
0.8769	High Similarity	NPC85702
0.8621	High Similarity	NPC27324
0.8621	High Similarity	NPC268676
0.8615	High Similarity	NPC473493
0.8454	Intermediate Similarity	NPC475619
0.8077	Intermediate Similarity	NPC287795
0.7717	Intermediate Similarity	NPC326479
0.7581	Intermediate Similarity	NPC46359
0.7554	Intermediate Similarity	NPC214106
0.7554	Intermediate Similarity	NPC26491
0.7513	Intermediate Similarity	NPC67551
0.7461	Intermediate Similarity	NPC117027
0.7363	Intermediate Similarity	NPC227582
0.736	Intermediate Similarity	NPC473666
0.734	Intermediate Similarity	NPC252338
0.7321	Intermediate Similarity	NPC82370
0.7317	Intermediate Similarity	NPC134848
0.73	Intermediate Similarity	NPC472210
0.73	Intermediate Similarity	NPC81802
0.73	Intermediate Similarity	NPC269886
0.73	Intermediate Similarity	NPC472295
0.73	Intermediate Similarity	NPC247735
0.7273	Intermediate Similarity	NPC321708
0.7241	Intermediate Similarity	NPC131887
0.7225	Intermediate Similarity	NPC469743
0.7216	Intermediate Similarity	NPC55772
0.7214	Intermediate Similarity	NPC304203
0.7192	Intermediate Similarity	NPC141454
0.7189	Intermediate Similarity	NPC229893
0.7186	Intermediate Similarity	NPC221873
0.7164	Intermediate Similarity	NPC472292
0.7157	Intermediate Similarity	NPC67288
0.7143	Intermediate Similarity	NPC472293
0.7129	Intermediate Similarity	NPC267343
0.7128	Intermediate Similarity	NPC219336
0.7115	Intermediate Similarity	NPC132539
0.7105	Intermediate Similarity	NPC115232
0.7103	Intermediate Similarity	NPC36405
0.7101	Intermediate Similarity	NPC137589
0.7101	Intermediate Similarity	NPC476073
0.7094	Intermediate Similarity	NPC202812
0.7085	Intermediate Similarity	NPC160381
0.7077	Intermediate Similarity	NPC183662
0.7077	Intermediate Similarity	NPC217372
0.7077	Intermediate Similarity	NPC15573
0.7077	Intermediate Similarity	NPC111275
0.7067	Intermediate Similarity	NPC165599
0.7065	Intermediate Similarity	NPC154339
0.7059	Intermediate Similarity	NPC11445
0.7056	Intermediate Similarity	NPC474412
0.7039	Intermediate Similarity	NPC74413
0.7039	Intermediate Similarity	NPC472296
0.7039	Intermediate Similarity	NPC472297
0.7031	Intermediate Similarity	NPC78020
0.703	Intermediate Similarity	NPC476460
0.7026	Intermediate Similarity	NPC267885
0.7026	Intermediate Similarity	NPC151635
0.7019	Intermediate Similarity	NPC260900
0.7015	Intermediate Similarity	NPC175474
0.701	Intermediate Similarity	NPC195239
0.701	Intermediate Similarity	NPC157828
0.701	Intermediate Similarity	NPC252572
0.7009	Intermediate Similarity	NPC70155
0.7009	Intermediate Similarity	NPC31700
0.7	Intermediate Similarity	NPC235684
0.7	Intermediate Similarity	NPC62749
0.6995	Remote Similarity	NPC471943
0.6991	Remote Similarity	NPC249428
0.699	Remote Similarity	NPC171317
0.6985	Remote Similarity	NPC477003
0.6974	Remote Similarity	NPC110500
0.6974	Remote Similarity	NPC149155
0.6974	Remote Similarity	NPC203468
0.6967	Remote Similarity	NPC477065
0.6954	Remote Similarity	NPC126709
0.6954	Remote Similarity	NPC248041
0.6919	Remote Similarity	NPC91179
0.6919	Remote Similarity	NPC469896
0.6915	Remote Similarity	NPC99428
0.6908	Remote Similarity	NPC52557
0.6904	Remote Similarity	NPC284775
0.6901	Remote Similarity	NPC478158
0.6901	Remote Similarity	NPC162860
0.6901	Remote Similarity	NPC284102
0.6897	Remote Similarity	NPC206967
0.6897	Remote Similarity	NPC329858
0.6897	Remote Similarity	NPC314333
0.6895	Remote Similarity	NPC276657
0.6893	Remote Similarity	NPC472116
0.689	Remote Similarity	NPC471944
0.6887	Remote Similarity	NPC54420
0.6887	Remote Similarity	NPC244741
0.6884	Remote Similarity	NPC12344
0.6881	Remote Similarity	NPC278434
0.6875	Remote Similarity	NPC293917
0.6872	Remote Similarity	NPC473376
0.6869	Remote Similarity	NPC283219
0.6869	Remote Similarity	NPC213468
0.6857	Remote Similarity	NPC193761
0.6853	Remote Similarity	NPC178858
0.6847	Remote Similarity	NPC196251
0.6847	Remote Similarity	NPC111602
0.6847	Remote Similarity	NPC63199
0.6847	Remote Similarity	NPC102338
0.6845	Remote Similarity	NPC19692
0.6845	Remote Similarity	NPC220151
0.6842	Remote Similarity	NPC249150
0.6842	Remote Similarity	NPC313985
0.6842	Remote Similarity	NPC195461
0.6842	Remote Similarity	NPC79129
0.6842	Remote Similarity	NPC81654
0.6842	Remote Similarity	NPC15801
0.6842	Remote Similarity	NPC49196
0.684	Remote Similarity	NPC471191
0.6835	Remote Similarity	NPC312645
0.6827	Remote Similarity	NPC50503
0.6825	Remote Similarity	NPC317701
0.6822	Remote Similarity	NPC271862
0.6818	Remote Similarity	NPC145885
0.6818	Remote Similarity	NPC14113
0.6818	Remote Similarity	NPC84827
0.6814	Remote Similarity	NPC472112
0.6814	Remote Similarity	NPC83111
0.6814	Remote Similarity	NPC324091
0.6812	Remote Similarity	NPC79356
0.6812	Remote Similarity	NPC102592
0.6806	Remote Similarity	NPC110182
0.6804	Remote Similarity	NPC264285
0.6794	Remote Similarity	NPC241024
0.6789	Remote Similarity	NPC285469
0.6782	Remote Similarity	NPC133003
0.6777	Remote Similarity	NPC476874
0.6776	Remote Similarity	NPC39679
0.6774	Remote Similarity	NPC89508
0.6774	Remote Similarity	NPC472291
0.6765	Remote Similarity	NPC213629
0.6762	Remote Similarity	NPC214428
0.6756	Remote Similarity	NPC33949
0.6749	Remote Similarity	NPC315555
0.6748	Remote Similarity	NPC55493
0.6748	Remote Similarity	NPC472113
0.6745	Remote Similarity	NPC98715
0.6744	Remote Similarity	NPC107077
0.6744	Remote Similarity	NPC223791
0.6743	Remote Similarity	NPC478157
0.6739	Remote Similarity	NPC101130
0.6739	Remote Similarity	NPC58268
0.6739	Remote Similarity	NPC114033
0.6739	Remote Similarity	NPC129412
0.6728	Remote Similarity	NPC153980
0.6728	Remote Similarity	NPC6865
0.6727	Remote Similarity	NPC477714
0.6718	Remote Similarity	NPC160105
0.6716	Remote Similarity	NPC472323
0.6715	Remote Similarity	NPC326422
0.6714	Remote Similarity	NPC314648
0.6711	Remote Similarity	NPC469720
0.6701	Remote Similarity	NPC6982
0.6701	Remote Similarity	NPC21174
0.6701	Remote Similarity	NPC8104
0.6701	Remote Similarity	NPC271797
0.6699	Remote Similarity	NPC138370
0.6698	Remote Similarity	NPC162730
0.6698	Remote Similarity	NPC474116
0.6698	Remote Similarity	NPC127677
0.6698	Remote Similarity	NPC258062
0.6697	Remote Similarity	NPC54744
0.6696	Remote Similarity	NPC267853
0.6683	Remote Similarity	NPC276517
0.6682	Remote Similarity	NPC472285
0.6682	Remote Similarity	NPC16352
0.6682	Remote Similarity	NPC87413
0.6682	Remote Similarity	NPC72956
0.6667	Remote Similarity	NPC314603
0.6667	Remote Similarity	NPC15840
0.6667	Remote Similarity	NPC76982
0.6667	Remote Similarity	NPC473747
0.6667	Remote Similarity	NPC244897
0.6667	Remote Similarity	NPC477044
0.6667	Remote Similarity	NPC477041
0.6667	Remote Similarity	NPC306376
0.6667	Remote Similarity	NPC88110
0.6652	Remote Similarity	NPC473310
0.6651	Remote Similarity	NPC87856
0.6651	Remote Similarity	NPC46225
0.6651	Remote Similarity	NPC75634
0.6651	Remote Similarity	NPC151976
0.6651	Remote Similarity	NPC225821
0.6651	Remote Similarity	NPC314297
0.6651	Remote Similarity	NPC315545
0.665	Remote Similarity	NPC472119
0.665	Remote Similarity	NPC59269
0.665	Remote Similarity	NPC472294
0.6649	Remote Similarity	NPC16667
0.6637	Remote Similarity	NPC2395
0.6637	Remote Similarity	NPC476491
0.6636	Remote Similarity	NPC74969
0.6636	Remote Similarity	NPC204491

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 NPC195457 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	595
0.2-0.3	856
0.3-0.4	2480
0.4-0.5	2851
0.5-0.6	1781
0.6-0.7	334
0.7-0.8	24
0.8-0.85	5
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9149	High Similarity	NPD7941	Phase 3
0.9062	High Similarity	NPD8160	Phase 2
0.8711	High Similarity	NPD8096	Phase 3
0.8711	High Similarity	NPD8097	Phase 3
0.8708	High Similarity	NPD7865	Approved
0.8542	High Similarity	NPD8098	Approved
0.8446	Intermediate Similarity	NPD56	Approved
0.8446	Intermediate Similarity	NPD8283	Approved
0.8446	Intermediate Similarity	NPD8282	Approved
0.8041	Intermediate Similarity	NPD7946	Pre-registration
0.8	Intermediate Similarity	NPD7869	Discontinued
0.7967	Intermediate Similarity	NPD7866	Approved
0.7861	Intermediate Similarity	NPD8423	Phase 2
0.7861	Intermediate Similarity	NPD8399	Phase 1
0.7814	Intermediate Similarity	NPD7864	Approved
0.7717	Intermediate Similarity	NPD7863	Approved
0.7676	Intermediate Similarity	NPD2844	Phase 3
0.7363	Intermediate Similarity	NPD7882	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD8396	Approved
0.7206	Intermediate Similarity	NPD8395	Approved
0.7115	Intermediate Similarity	NPD5426	Phase 3
0.7114	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1573	Approved
0.7083	Intermediate Similarity	NPD1575	Approved
0.7062	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2091	Phase 2
0.6985	Remote Similarity	NPD2096	Phase 2
0.6974	Remote Similarity	NPD482	Approved
0.6957	Remote Similarity	NPD6999	Discontinued
0.6957	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5901	Discontinued
0.6935	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2092	Phase 2
0.6935	Remote Similarity	NPD2095	Phase 2
0.6935	Remote Similarity	NPD2094	Phase 2
0.6931	Remote Similarity	NPD1534	Approved
0.6923	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4499	Approved
0.6881	Remote Similarity	NPD7878	Phase 2
0.6881	Remote Similarity	NPD4948	Discontinued
0.6875	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1631	Approved
0.6869	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5003	Discontinued
0.6854	Remote Similarity	NPD7666	Phase 3
0.6854	Remote Similarity	NPD7665	Phase 2
0.6842	Remote Similarity	NPD4600	Approved
0.6842	Remote Similarity	NPD4601	Approved
0.6792	Remote Similarity	NPD6987	Phase 1
0.6776	Remote Similarity	NPD2509	Approved
0.6776	Remote Similarity	NPD2510	Approved
0.6761	Remote Similarity	NPD7001	Phase 3
0.6759	Remote Similarity	NPD7470	Discontinued
0.6751	Remote Similarity	NPD750	Phase 2
0.6744	Remote Similarity	NPD4506	Discontinued
0.6728	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4852	Phase 2
0.6719	Remote Similarity	NPD1630	Approved
0.6716	Remote Similarity	NPD3178	Discontinued
0.6714	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD3947	Discontinued
0.6713	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5473	Discontinued
0.6667	Remote Similarity	NPD6176	Phase 1
0.6667	Remote Similarity	NPD6595	Phase 3
0.6651	Remote Similarity	NPD8322	Phase 2
0.6651	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6165	Phase 2
0.6637	Remote Similarity	NPD6164	Phase 2
0.6622	Remote Similarity	NPD6770	Approved
0.662	Remote Similarity	NPD8073	Approved
0.6617	Remote Similarity	NPD1587	Approved
0.6615	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6995	Phase 1
0.6605	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2008	Discontinued
0.6605	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4501	Approved
0.6604	Remote Similarity	NPD4500	Approved
0.6599	Remote Similarity	NPD1343	Approved
0.6591	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8072	Approved
0.6588	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.657	Remote Similarity	NPD2565	Phase 2
0.657	Remote Similarity	NPD2564	Approved
0.6566	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6733	Discontinued
0.6559	Remote Similarity	NPD1592	Phase 3
0.6558	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7688	Phase 1
0.6546	Remote Similarity	NPD2214	Approved
0.6546	Remote Similarity	NPD2213	Approved
0.6538	Remote Similarity	NPD2336	Approved
0.6537	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7957	Phase 1
0.652	Remote Similarity	NPD3318	Approved
0.652	Remote Similarity	NPD3319	Phase 1
0.652	Remote Similarity	NPD3320	Approved
0.652	Remote Similarity	NPD7711	Discontinued
0.6516	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.65	Remote Similarity	NPD2411	Approved
0.65	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD3835	Phase 3
0.6492	Remote Similarity	NPD3833	Phase 3
0.6488	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4851	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3394	Approved
0.6486	Remote Similarity	NPD3389	Approved
0.6486	Remote Similarity	NPD3393	Approved
0.6484	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6486	Approved
0.6468	Remote Similarity	NPD2443	Approved
0.6468	Remote Similarity	NPD6487	Approved
0.6468	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7232	Discontinued
0.6468	Remote Similarity	NPD1586	Approved
0.6468	Remote Similarity	NPD2442	Approved
0.6465	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD8386	Phase 2
0.6453	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8403	Phase 1
0.6447	Remote Similarity	NPD5138	Approved
0.6447	Remote Similarity	NPD5140	Approved
0.6441	Remote Similarity	NPD7970	Approved
0.6441	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1600	Suspended
0.6436	Remote Similarity	NPD5471	Phase 3
0.6429	Remote Similarity	NPD1896	Approved
0.6425	Remote Similarity	NPD7454	Approved
0.6425	Remote Similarity	NPD7455	Approved
0.6422	Remote Similarity	NPD7789	Approved
0.6422	Remote Similarity	NPD7951	Approved
0.6422	Remote Similarity	NPD7950	Approved
0.6422	Remote Similarity	NPD7791	Approved
0.6422	Remote Similarity	NPD7790	Approved
0.6422	Remote Similarity	NPD7953	Approved
0.6422	Remote Similarity	NPD7952	Approved
0.6419	Remote Similarity	NPD5017	Discontinued
0.6415	Remote Similarity	NPD2307	Discontinued
0.6408	Remote Similarity	NPD721	Approved
0.6396	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3773	Approved
0.6389	Remote Similarity	NPD3775	Approved
0.6389	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3774	Approved
0.6384	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD484	Approved
0.6368	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD53	Approved
0.6355	Remote Similarity	NPD4397	Phase 1
0.6355	Remote Similarity	NPD7777	Approved
0.6355	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7778	Approved
0.6351	Remote Similarity	NPD5505	Discontinued
0.6351	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7731	Approved
0.6348	Remote Similarity	NPD7730	Approved
0.6338	Remote Similarity	NPD1871	Approved
0.6335	Remote Similarity	NPD4051	Discontinued
0.633	Remote Similarity	NPD8115	Approved
0.633	Remote Similarity	NPD8114	Approved
0.6329	Remote Similarity	NPD6178	Phase 3
0.6318	Remote Similarity	NPD1325	Approved
0.6318	Remote Similarity	NPD6376	Discontinued
0.6318	Remote Similarity	NPD1326	Approved
0.6316	Remote Similarity	NPD8431	Approved
0.6311	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD3746	Discontinued
0.6306	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7568	Phase 1
0.63	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2305	Discontinued
0.6293	Remote Similarity	NPD7824	Approved
0.6291	Remote Similarity	NPD7619	Phase 3
0.6291	Remote Similarity	NPD4602	Approved
0.6291	Remote Similarity	NPD7618	Phase 3
0.629	Remote Similarity	NPD2408	Discontinued
0.6288	Remote Similarity	NPD7661	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6267	Discontinued
0.6284	Remote Similarity	NPD2920	Discontinued
0.628	Remote Similarity	NPD4345	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