NPASS Compound

Structure

CID214988 OpenBabel06191716002D 44 46 0 0 1 0 0 0 0 0999 V2000 3.0976 -4.0976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2317 -4.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0976 -3.0977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3167 -3.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3658 -4.0976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2317 -2.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3170 -3.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5833 0.1320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4246 -1.1552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3264 -0.5369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1678 -1.8241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8168 -3.8756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8892 0.4918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1482 2.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2866 1.1613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3658 -3.0977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6324 -0.1771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1187 -1.5150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6479 -2.2674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9758 0.0850 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0001 -1.7320 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3088 0.9528 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0620 1.6679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3606 1.6954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6693 -2.4759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8712 -0.9094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5002 -0.8663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3167 -4.7411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3164 -4.7408 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8170 -5.6070 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.8166 -3.8754 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3386 1.4871 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1662 0.6727 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9568 -1.3166 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9998 -1.7323 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 1.2860 2.1611 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8619 -2.1839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8711 2.2555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0521 2.6466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3605 -3.4270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6802 -1.4972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5002 -0.8664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 4 7 1 0 0 0 0 4 12 1 0 0 0 0 5 17 2 0 0 0 0 6 17 1 0 0 0 0 8 10 1 0 0 0 0 8 18 2 0 0 0 0 9 11 2 0 0 0 0 9 18 1 0 0 0 0 10 19 2 0 0 0 0 11 19 1 0 0 0 0 12 32 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 24 1 0 0 0 0 15 33 1 0 0 0 0 16 38 1 0 0 0 0 19 39 1 0 0 0 0 20 7 1 6 0 0 0 20 26 1 0 0 0 0 20 35 1 0 0 0 0 21 14 1 6 0 0 0 21 27 1 0 0 0 0 21 34 1 0 0 0 0 22 13 1 6 0 0 0 22 28 1 0 0 0 0 22 36 1 0 0 0 0 23 16 1 6 0 0 0 23 25 1 0 0 0 0 23 37 1 0 0 0 0 24 34 2 3 0 0 0 24 40 1 0 0 0 0 25 33 2 3 0 0 0 25 41 1 0 0 0 0 26 36 2 3 0 0 0 26 42 1 0 0 0 0 27 35 2 3 0 0 0 27 43 1 0 0 0 0 28 37 2 3 0 0 0 28 44 1 0 0 0 0 29 30 2 0 0 0 0 29 31 1 0 0 0 0 29 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	610.29
Volume:	602.339
LogP:	-1.177
LogD:	-0.352
LogS:	-2.622
# Rotatable Bonds:	10
TPSA:	247.86
# H-Bond Aceptor:	15
# H-Bond Donor:	11
# Rings:	3
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.082
Synthetic Accessibility Score:	4.547
Fsp3:	0.379
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:	-7.077
MDCK Permeability:	3.944302079617046e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.928
Human Intestinal Absorption (HIA):	0.75
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	28.24530029296875%
Volume Distribution (VD):	0.351
Pgp-substrate:	58.69597244262695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.238
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.17
CYP3A4-inhibitor:	0.043
CYP3A4-substrate:	0.008

ADMET: Excretion

Clearance (CL):	1.983
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.152
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.657
Maximum Recommended Daily Dose:	0.34
Skin Sensitization:	0.195
Carcinogencity:	0.118
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.354

Download Data

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

Natural Product: NPC214988

Natural Product ID:	NPC214988
*Common Name:**	Segetalin H
IUPAC Name:	2-[3-[(2S,5S,8S,14S)-5-benzyl-8-(hydroxymethyl)-14-[(4-hydroxyphenyl)methyl]-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentazacyclopentadec-2-yl]propyl]guanidine
Synonyms:	Segetalin H
Standard InCHIKey:	MFTFAHIWRYRALU-MLCQCVOFSA-N
Standard InCHI:	InChI=1S/C29H38N8O7/c30-29(31)32-12-4-7-20-26(42)36-22(13-17-5-2-1-3-6-17)28(44)37-23(16-38)25(41)33-15-24(40)34-21(27(43)35-20)14-18-8-10-19(39)11-9-18/h1-3,5-6,8-11,20-23,38-39H,4,7,12-16H2,(H,33,41)(H,34,40)(H,35,43)(H,36,42)(H,37,44)(H4,30,31,32)/t20-,21-,22-,23-/m0/s1
SMILES:	OC[C@@H]1N=C(O)[C@H](Cc2ccccc2)N=C(O)[C@H](CCCNC(=N)N)N=C([C@@H](N=C(CN=C1O)O)Cc1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL384334
PubChem CID:	10054463
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*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
NPO40525	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[9157189]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30164	Vaccaria segetalis	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6752	Melandryum firmum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TM-MC]
NPO829	Vaccaria hispanica	Species	Caryophyllaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	54.8	mg	PMID[516824]

☑ 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 NPC214988 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	208
0.1-0.2	1492
0.2-0.3	10701
0.3-0.4	7672
0.4-0.5	14440
0.5-0.6	6898
0.6-0.7	1057
0.7-0.8	208
0.8-0.85	13
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.969	High Similarity	NPC267237
0.9259	High Similarity	NPC168861
0.8777	High Similarity	NPC326241
0.8561	High Similarity	NPC48202
0.8321	Intermediate Similarity	NPC283760
0.8129	Intermediate Similarity	NPC280022
0.8038	Intermediate Similarity	NPC17698
0.803	Intermediate Similarity	NPC311737
0.803	Intermediate Similarity	NPC38458
0.8015	Intermediate Similarity	NPC317254
0.8	Intermediate Similarity	NPC326966
0.7962	Intermediate Similarity	NPC198254
0.7962	Intermediate Similarity	NPC274198
0.7955	Intermediate Similarity	NPC82963
0.7902	Intermediate Similarity	NPC64205
0.7888	Intermediate Similarity	NPC97526
0.7888	Intermediate Similarity	NPC119652
0.7862	Intermediate Similarity	NPC475532
0.7857	Intermediate Similarity	NPC271808
0.7857	Intermediate Similarity	NPC325651
0.7848	Intermediate Similarity	NPC276506
0.7812	Intermediate Similarity	NPC165285
0.7791	Intermediate Similarity	NPC473404
0.7764	Intermediate Similarity	NPC196243
0.7756	Intermediate Similarity	NPC22014
0.7679	Intermediate Similarity	NPC240130
0.7679	Intermediate Similarity	NPC61332
0.7673	Intermediate Similarity	NPC129486
0.7671	Intermediate Similarity	NPC197045
0.7669	Intermediate Similarity	NPC118202
0.7655	Intermediate Similarity	NPC237227
0.7628	Intermediate Similarity	NPC469243
0.7622	Intermediate Similarity	NPC153554
0.7619	Intermediate Similarity	NPC476989
0.7615	Intermediate Similarity	NPC96224
0.7615	Intermediate Similarity	NPC24101
0.7612	Intermediate Similarity	NPC213
0.7612	Intermediate Similarity	NPC10286
0.7566	Intermediate Similarity	NPC473491
0.7564	Intermediate Similarity	NPC244336
0.7562	Intermediate Similarity	NPC66490
0.756	Intermediate Similarity	NPC94862
0.7557	Intermediate Similarity	NPC258056
0.7544	Intermediate Similarity	NPC302715
0.7532	Intermediate Similarity	NPC476742
0.7516	Intermediate Similarity	NPC475544
0.7515	Intermediate Similarity	NPC475564
0.7515	Intermediate Similarity	NPC102959
0.7515	Intermediate Similarity	NPC170302
0.7515	Intermediate Similarity	NPC475409
0.75	Intermediate Similarity	NPC477638
0.75	Intermediate Similarity	NPC473546
0.75	Intermediate Similarity	NPC477632
0.75	Intermediate Similarity	NPC474149
0.75	Intermediate Similarity	NPC137096
0.75	Intermediate Similarity	NPC197921
0.7484	Intermediate Similarity	NPC476741
0.7484	Intermediate Similarity	NPC223207
0.7482	Intermediate Similarity	NPC474862
0.7481	Intermediate Similarity	NPC153690
0.7471	Intermediate Similarity	NPC60516
0.7462	Intermediate Similarity	NPC231705
0.7457	Intermediate Similarity	NPC329295
0.7451	Intermediate Similarity	NPC476743
0.745	Intermediate Similarity	NPC189724
0.745	Intermediate Similarity	NPC83289
0.745	Intermediate Similarity	NPC469360
0.745	Intermediate Similarity	NPC212850
0.745	Intermediate Similarity	NPC91953
0.7448	Intermediate Similarity	NPC208757
0.7438	Intermediate Similarity	NPC304074
0.7438	Intermediate Similarity	NPC471771
0.7438	Intermediate Similarity	NPC290755
0.7424	Intermediate Similarity	NPC290566
0.7424	Intermediate Similarity	NPC145638
0.741	Intermediate Similarity	NPC273830
0.7405	Intermediate Similarity	NPC142297
0.7403	Intermediate Similarity	NPC476744
0.7391	Intermediate Similarity	NPC268572
0.7386	Intermediate Similarity	NPC245974
0.7376	Intermediate Similarity	NPC307020
0.7372	Intermediate Similarity	NPC473580
0.7372	Intermediate Similarity	NPC244509
0.7368	Intermediate Similarity	NPC16188
0.7357	Intermediate Similarity	NPC27581
0.7353	Intermediate Similarity	NPC96275
0.7329	Intermediate Similarity	NPC244866
0.7301	Intermediate Similarity	NPC46009
0.7292	Intermediate Similarity	NPC477839
0.7267	Intermediate Similarity	NPC477636
0.7267	Intermediate Similarity	NPC51047
0.7261	Intermediate Similarity	NPC476268
0.7255	Intermediate Similarity	NPC247298
0.7252	Intermediate Similarity	NPC211551
0.7244	Intermediate Similarity	NPC262166
0.7244	Intermediate Similarity	NPC202198
0.7231	Intermediate Similarity	NPC178902
0.7222	Intermediate Similarity	NPC236347
0.7222	Intermediate Similarity	NPC322366
0.7222	Intermediate Similarity	NPC323775
0.7212	Intermediate Similarity	NPC306804
0.7203	Intermediate Similarity	NPC95733
0.7203	Intermediate Similarity	NPC62101
0.7194	Intermediate Similarity	NPC85276
0.7194	Intermediate Similarity	NPC122009
0.7184	Intermediate Similarity	NPC477631
0.7181	Intermediate Similarity	NPC6570
0.7178	Intermediate Similarity	NPC328649
0.7178	Intermediate Similarity	NPC302597
0.7175	Intermediate Similarity	NPC477552
0.7175	Intermediate Similarity	NPC477550
0.7172	Intermediate Similarity	NPC311753
0.717	Intermediate Similarity	NPC326349
0.717	Intermediate Similarity	NPC323336
0.7169	Intermediate Similarity	NPC471165
0.716	Intermediate Similarity	NPC63931
0.7153	Intermediate Similarity	NPC318965
0.7153	Intermediate Similarity	NPC29477
0.7143	Intermediate Similarity	NPC43275
0.7143	Intermediate Similarity	NPC241794
0.7143	Intermediate Similarity	NPC473724
0.7134	Intermediate Similarity	NPC56685
0.7132	Intermediate Similarity	NPC125732
0.7126	Intermediate Similarity	NPC50016
0.7122	Intermediate Similarity	NPC283468
0.7117	Intermediate Similarity	NPC247251
0.7117	Intermediate Similarity	NPC61004
0.7114	Intermediate Similarity	NPC314835
0.711	Intermediate Similarity	NPC246591
0.7108	Intermediate Similarity	NPC273755
0.7105	Intermediate Similarity	NPC323123
0.7095	Intermediate Similarity	NPC307123
0.7095	Intermediate Similarity	NPC469443
0.7095	Intermediate Similarity	NPC471953
0.7095	Intermediate Similarity	NPC247018
0.7095	Intermediate Similarity	NPC97870
0.7095	Intermediate Similarity	NPC477551
0.7091	Intermediate Similarity	NPC475204
0.7091	Intermediate Similarity	NPC475123
0.7075	Intermediate Similarity	NPC474091
0.7073	Intermediate Similarity	NPC294516
0.7073	Intermediate Similarity	NPC107938
0.7063	Intermediate Similarity	NPC233926
0.7062	Intermediate Similarity	NPC477639
0.7055	Intermediate Similarity	NPC296712
0.7054	Intermediate Similarity	NPC107619
0.7048	Intermediate Similarity	NPC230611
0.7045	Intermediate Similarity	NPC147000
0.7045	Intermediate Similarity	NPC150254
0.7045	Intermediate Similarity	NPC304761
0.7045	Intermediate Similarity	NPC226778
0.7041	Intermediate Similarity	NPC194671
0.7041	Intermediate Similarity	NPC45037
0.7041	Intermediate Similarity	NPC269750
0.7039	Intermediate Similarity	NPC211468
0.7039	Intermediate Similarity	NPC219233
0.7039	Intermediate Similarity	NPC170170
0.7029	Intermediate Similarity	NPC470728
0.7027	Intermediate Similarity	NPC45191
0.7023	Intermediate Similarity	NPC91461
0.7023	Intermediate Similarity	NPC7686
0.7023	Intermediate Similarity	NPC40258
0.7021	Intermediate Similarity	NPC319950
0.702	Intermediate Similarity	NPC313694
0.702	Intermediate Similarity	NPC242159
0.7014	Intermediate Similarity	NPC211218
0.7013	Intermediate Similarity	NPC266741
0.7006	Intermediate Similarity	NPC248670
0.7006	Intermediate Similarity	NPC137627
0.6988	Remote Similarity	NPC40234
0.6981	Remote Similarity	NPC47672
0.698	Remote Similarity	NPC274732
0.6972	Remote Similarity	NPC263835
0.6972	Remote Similarity	NPC115627
0.6972	Remote Similarity	NPC118522
0.6972	Remote Similarity	NPC169207
0.697	Remote Similarity	NPC68055
0.6968	Remote Similarity	NPC314114
0.6968	Remote Similarity	NPC81026
0.6964	Remote Similarity	NPC473402
0.6964	Remote Similarity	NPC158277
0.6964	Remote Similarity	NPC26108
0.6964	Remote Similarity	NPC279871
0.6962	Remote Similarity	NPC233702
0.6954	Remote Similarity	NPC6913
0.6947	Remote Similarity	NPC155847
0.6947	Remote Similarity	NPC289381
0.6947	Remote Similarity	NPC213730
0.6946	Remote Similarity	NPC89831
0.6929	Remote Similarity	NPC281686
0.6929	Remote Similarity	NPC188867
0.6929	Remote Similarity	NPC106551
0.6923	Remote Similarity	NPC284078
0.6923	Remote Similarity	NPC311658
0.6918	Remote Similarity	NPC5194
0.6918	Remote Similarity	NPC261934
0.6918	Remote Similarity	NPC477937
0.6913	Remote Similarity	NPC114102
0.6913	Remote Similarity	NPC475735
0.691	Remote Similarity	NPC80514

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 NPC214988 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	120
0.1-0.2	480
0.2-0.3	939
0.3-0.4	1570
0.4-0.5	3453
0.5-0.6	2046
0.6-0.7	454
0.7-0.8	82
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8841	High Similarity	NPD6809	Clinical (unspecified phase)
0.8786	High Similarity	NPD7066	Clinical (unspecified phase)
0.8514	High Similarity	NPD7495	Discontinued
0.8514	High Similarity	NPD8019	Approved
0.8299	Intermediate Similarity	NPD7523	Phase 3
0.8235	Intermediate Similarity	NPD7451	Discontinued
0.8074	Intermediate Similarity	NPD2562	Approved
0.8074	Intermediate Similarity	NPD2561	Approved
0.7972	Intermediate Similarity	NPD3555	Approved
0.7972	Intermediate Similarity	NPD3554	Approved
0.7972	Intermediate Similarity	NPD3552	Approved
0.7972	Intermediate Similarity	NPD3553	Approved
0.7929	Intermediate Similarity	NPD3136	Phase 2
0.7919	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD2568	Approved
0.7808	Intermediate Similarity	NPD7978	Discontinued
0.7778	Intermediate Similarity	NPD5314	Approved
0.7771	Intermediate Similarity	NPD8303	Discontinued
0.7761	Intermediate Similarity	NPD318	Approved
0.7761	Intermediate Similarity	NPD317	Approved
0.7698	Intermediate Similarity	NPD5310	Approved
0.7698	Intermediate Similarity	NPD5311	Approved
0.7692	Intermediate Similarity	NPD6407	Approved
0.7692	Intermediate Similarity	NPD6405	Approved
0.7671	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3055	Approved
0.7643	Intermediate Similarity	NPD3053	Approved
0.7639	Intermediate Similarity	NPD3062	Approved
0.7639	Intermediate Similarity	NPD3059	Approved
0.7639	Intermediate Similarity	NPD3061	Approved
0.763	Intermediate Similarity	NPD16	Approved
0.763	Intermediate Similarity	NPD856	Approved
0.7619	Intermediate Similarity	NPD7450	Phase 2
0.75	Intermediate Similarity	NPD9615	Approved
0.75	Intermediate Similarity	NPD9613	Approved
0.75	Intermediate Similarity	NPD9616	Approved
0.7467	Intermediate Similarity	NPD2459	Approved
0.7467	Intermediate Similarity	NPD2460	Phase 3
0.7467	Intermediate Similarity	NPD2458	Approved
0.7445	Intermediate Similarity	NPD316	Approved
0.7424	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3052	Approved
0.7415	Intermediate Similarity	NPD3054	Approved
0.7403	Intermediate Similarity	NPD7303	Discontinued
0.7394	Intermediate Similarity	NPD1133	Approved
0.7394	Intermediate Similarity	NPD1134	Approved
0.7394	Intermediate Similarity	NPD1131	Approved
0.7394	Intermediate Similarity	NPD1129	Approved
0.7394	Intermediate Similarity	NPD1135	Approved
0.7379	Intermediate Similarity	NPD601	Approved
0.7379	Intermediate Similarity	NPD597	Approved
0.7379	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD598	Approved
0.7376	Intermediate Similarity	NPD4659	Approved
0.7343	Intermediate Similarity	NPD599	Approved
0.7343	Intermediate Similarity	NPD602	Approved
0.7338	Intermediate Similarity	NPD2874	Phase 2
0.7329	Intermediate Similarity	NPD1136	Approved
0.7329	Intermediate Similarity	NPD1132	Approved
0.7329	Intermediate Similarity	NPD1130	Approved
0.7329	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9610	Approved
0.7308	Intermediate Similarity	NPD9608	Approved
0.7297	Intermediate Similarity	NPD817	Approved
0.7297	Intermediate Similarity	NPD823	Approved
0.7286	Intermediate Similarity	NPD3421	Phase 3
0.7279	Intermediate Similarity	NPD9618	Approved
0.7279	Intermediate Similarity	NPD9614	Approved
0.7273	Intermediate Similarity	NPD4103	Phase 2
0.7273	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7617	Discontinued
0.7267	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD3060	Approved
0.7222	Intermediate Similarity	NPD9620	Approved
0.7222	Intermediate Similarity	NPD9621	Approved
0.7222	Intermediate Similarity	NPD9619	Approved
0.7222	Intermediate Similarity	NPD858	Approved
0.7222	Intermediate Similarity	NPD859	Approved
0.7214	Intermediate Similarity	NPD7342	Discontinued
0.72	Intermediate Similarity	NPD7425	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD5303	Approved
0.7194	Intermediate Similarity	NPD5304	Approved
0.717	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD8154	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3638	Discontinued
0.7124	Intermediate Similarity	NPD2211	Approved
0.7124	Intermediate Similarity	NPD2209	Approved
0.7115	Intermediate Similarity	NPD6419	Discontinued
0.7115	Intermediate Similarity	NPD3985	Discontinued
0.7095	Intermediate Similarity	NPD1423	Approved
0.7092	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD2234	Approved
0.708	Intermediate Similarity	NPD2228	Approved
0.708	Intermediate Similarity	NPD2229	Approved
0.707	Intermediate Similarity	NPD6078	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD309	Approved
0.7045	Intermediate Similarity	NPD311	Approved
0.7045	Intermediate Similarity	NPD310	Approved
0.7045	Intermediate Similarity	NPD315	Approved
0.7045	Intermediate Similarity	NPD314	Approved
0.7045	Intermediate Similarity	NPD10	Approved
0.7032	Intermediate Similarity	NPD8131	Suspended
0.7014	Intermediate Similarity	NPD9622	Approved
0.7006	Intermediate Similarity	NPD3536	Discontinued
0.6987	Remote Similarity	NPD7554	Discontinued
0.698	Remote Similarity	NPD839	Approved
0.698	Remote Similarity	NPD840	Approved
0.698	Remote Similarity	NPD829	Discontinued
0.6978	Remote Similarity	NPD7508	Discontinued
0.6972	Remote Similarity	NPD9381	Approved
0.6972	Remote Similarity	NPD9384	Approved
0.6966	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD52	Approved
0.6962	Remote Similarity	NPD7526	Approved
0.6962	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3560	Approved
0.6933	Remote Similarity	NPD3556	Approved
0.6933	Remote Similarity	NPD3557	Approved
0.6933	Remote Similarity	NPD3558	Approved
0.6933	Remote Similarity	NPD6346	Approved
0.6929	Remote Similarity	NPD9568	Approved
0.6923	Remote Similarity	NPD1983	Approved
0.6923	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1980	Approved
0.6923	Remote Similarity	NPD1981	Approved
0.6903	Remote Similarity	NPD4162	Approved
0.6903	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD9379	Approved
0.6884	Remote Similarity	NPD9377	Approved
0.6875	Remote Similarity	NPD5267	Discontinued
0.6875	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2977	Approved
0.6871	Remote Similarity	NPD6283	Phase 2
0.6871	Remote Similarity	NPD2978	Approved
0.6863	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6380	Phase 1
0.6859	Remote Similarity	NPD3400	Discontinued
0.6852	Remote Similarity	NPD6072	Discontinued
0.6852	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8031	Discontinued
0.6839	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7153	Discontinued
0.6835	Remote Similarity	NPD6087	Phase 1
0.6832	Remote Similarity	NPD6056	Approved
0.6832	Remote Similarity	NPD6057	Approved
0.6831	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7485	Phase 3
0.6826	Remote Similarity	NPD7484	Phase 3
0.6815	Remote Similarity	NPD302	Approved
0.68	Remote Similarity	NPD8011	Discontinued
0.6795	Remote Similarity	NPD44	Approved
0.6795	Remote Similarity	NPD6364	Approved
0.6794	Remote Similarity	NPD9609	Approved
0.6794	Remote Similarity	NPD9612	Approved
0.6794	Remote Similarity	NPD9611	Approved
0.6792	Remote Similarity	NPD3645	Discontinued
0.6783	Remote Similarity	NPD1710	Approved
0.6783	Remote Similarity	NPD4093	Discontinued
0.6781	Remote Similarity	NPD4129	Approved
0.6772	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3845	Phase 1
0.6772	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD2195	Approved
0.6757	Remote Similarity	NPD2194	Approved
0.6755	Remote Similarity	NPD7477	Discontinued
0.675	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD2468	Approved
0.6748	Remote Similarity	NPD2469	Approved
0.6747	Remote Similarity	NPD8070	Approved
0.6733	Remote Similarity	NPD2372	Approved
0.6731	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4257	Approved
0.6731	Remote Similarity	NPD4256	Phase 2
0.6713	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7131	Phase 3
0.6692	Remote Similarity	NPD2934	Approved
0.6692	Remote Similarity	NPD2933	Approved
0.6689	Remote Similarity	NPD1819	Approved
0.6689	Remote Similarity	NPD1818	Approved
0.6689	Remote Similarity	NPD1039	Discontinued
0.6689	Remote Similarity	NPD3568	Approved
0.6689	Remote Similarity	NPD3567	Approved
0.6689	Remote Similarity	NPD1820	Approved
0.6689	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1817	Approved
0.6667	Remote Similarity	NPD2428	Approved
0.6667	Remote Similarity	NPD596	Approved
0.6667	Remote Similarity	NPD2429	Approved
0.6667	Remote Similarity	NPD593	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data