NPASS Compound

Structure

NPC246591 OpenBabel07101719402D 43 45 0 0 1 0 0 0 0 0999 V2000 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3443 2.2351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1363 3.2132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1691 2.2820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1473 2.0741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2953 1.9260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1853 3.5222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7872 0.3799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4563 1.1230 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9737 4.8094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.7168 4.1403 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1816 5.7875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5032 0.9479 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0226 4.5004 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -3.4344 0.9151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9680 -0.6994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 15 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 7 18 1 0 0 0 0 8 34 1 0 0 0 0 9 35 1 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 20 2 0 0 0 0 12 16 1 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 15 2 1 1 0 0 0 15 24 1 0 0 0 0 17 6 1 1 0 0 0 17 21 1 0 0 0 0 18 38 1 6 0 0 0 19 25 2 0 0 0 0 19 30 1 0 0 0 0 20 25 1 0 0 0 0 20 31 1 0 0 0 0 21 14 1 1 0 0 0 21 37 1 0 0 0 0 22 26 1 1 0 0 0 22 37 1 0 0 0 0 23 27 1 0 0 0 0 23 39 1 1 0 0 0 24 28 1 1 0 0 0 24 36 1 0 0 0 0 25 40 1 0 0 0 0 26 34 2 3 0 0 0 26 41 1 0 0 0 0 27 36 2 3 0 0 0 27 42 1 0 0 0 0 28 37 1 0 0 0 0 28 43 2 0 0 0 0 29 32 2 0 0 0 0 29 33 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	730.17
Volume:	623.305
LogP:	2.308
LogD:	1.104
LogS:	-3.601
# Rotatable Bonds:	16
TPSA:	203.6
# H-Bond Aceptor:	12
# H-Bond Donor:	9
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.09
Synthetic Accessibility Score:	4.589
Fsp3:	0.655
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:	-5.727
MDCK Permeability:	0.00010749483044492081
Pgp-inhibitor:	0.026
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.598
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.04

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	94.16114044189453%
Volume Distribution (VD):	0.662
Pgp-substrate:	10.50538444519043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.06
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.825
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	4.738
Half-life (T1/2):	0.325

ADMET: Toxicity

hERG Blockers:	0.159
Human Hepatotoxicity (H-HT):	0.687
Drug-inuced Liver Injury (DILI):	0.545
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.611
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.133
Carcinogencity:	0.057
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC246591

Natural Product ID:	NPC246591
*Common Name:**	Rel-(2S,3As,6R,7As)-1-((2R,3S)-2-((R)-3-(3,5-Dibromo-4-Hydroxyphenyl)-2-Hydroxypropanamido)-3-Methylpentanoyl)-N-(4-Guanidinobutyl)-6-Hydroxyoctahydro-1H-Indole-2-Carboxamide
IUPAC Name:	(2S,3aS,6R,7aS)-N-[4-(diaminomethylideneamino)butyl]-1-[(2R,3S)-2-[[(2R)-3-(3,5-dibromo-4-hydroxyphenyl)-2-hydroxypropanoyl]amino]-3-methylpentanoyl]-6-hydroxy-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxamide
Synonyms:
Standard InCHIKey:	HLHFYIIZYTUCEC-GPSFYHMWSA-N
Standard InCHI:	InChI=1S/C29H44Br2N6O6/c1-3-15(2)24(36-27(42)23(39)12-16-10-19(30)25(40)20(31)11-16)28(43)37-21-14-18(38)7-6-17(21)13-22(37)26(41)34-8-4-5-9-35-29(32)33/h10-11,15,17-18,21-24,38-40H,3-9,12-14H2,1-2H3,(H,34,41)(H,36,42)(H4,32,33,35)/t15-,17-,18+,21-,22-,23+,24+/m0/s1
SMILES:	CC[C@@H]([C@H](C(=O)N1[C@H]2C[C@H](O)CC[C@H]2C[C@H]1C(=NCCCCNC(=N)N)O)N=C([C@@H](Cc1cc(Br)c(c(c1)Br)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2207401
PubChem CID:	71452508
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:0004830] Dipeptides

*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
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11000050]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374973]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Einan Reservoir in Israel	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12141855]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18163584]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18558743]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18973386]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	water bloom of the cyanobacterium Microcystis aeruginosa	n.a.	n.a.	PMID[19650639]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	bloom material	Lake Kinneret, Israel	n.a.	PMID[22280481]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Kibbutz Geva, Israel	n.a.	PMID[23153007]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	Water Reservoir near Kibbutz Hafetz Haim, Israel	n.a.	PMID[23718637]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[24261937]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24642434]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24868986]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29405714]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	Bloom	n.a.	n.a.	PMID[29847132]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9249979]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9842728]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	n.a.	n.a.	n.a.	Database[Title]
NPO3288	Microcystis aeruginosa	Species	Microcystaceae	Bacteria	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
IC50	2

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	12900.0	nM	PMID[465693]
NPT2	Others	Unspecified		IC50	=	2300.0	nM	PMID[465693]

☑ 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 NPC246591 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	245
0.1-0.2	1311
0.2-0.3	9777
0.3-0.4	12259
0.4-0.5	16351
0.5-0.6	2191
0.6-0.7	442
0.7-0.8	104
0.8-0.85	9
0.85-0.9	5
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9709	High Similarity	NPC80514
0.9704	High Similarity	NPC96275
0.8913	High Similarity	NPC81845
0.8677	High Similarity	NPC295795
0.8547	High Similarity	NPC280022
0.8523	High Similarity	NPC97526
0.8523	High Similarity	NPC119652
0.8297	Intermediate Similarity	NPC94862
0.8284	Intermediate Similarity	NPC476268
0.8207	Intermediate Similarity	NPC51047
0.8162	Intermediate Similarity	NPC470728
0.7735	Intermediate Similarity	NPC89831
0.7692	Intermediate Similarity	NPC475532
0.7654	Intermediate Similarity	NPC63931
0.765	Intermediate Similarity	NPC165285
0.765	Intermediate Similarity	NPC17698
0.7641	Intermediate Similarity	NPC473450
0.7624	Intermediate Similarity	NPC129486
0.7604	Intermediate Similarity	NPC65714
0.7487	Intermediate Similarity	NPC471592
0.7487	Intermediate Similarity	NPC170302
0.7487	Intermediate Similarity	NPC102959
0.7487	Intermediate Similarity	NPC475564
0.7487	Intermediate Similarity	NPC475409
0.7486	Intermediate Similarity	NPC198254
0.7486	Intermediate Similarity	NPC276506
0.7486	Intermediate Similarity	NPC274198
0.7474	Intermediate Similarity	NPC477632
0.7474	Intermediate Similarity	NPC477638
0.7459	Intermediate Similarity	NPC471165
0.7448	Intermediate Similarity	NPC60516
0.7447	Intermediate Similarity	NPC473404
0.7429	Intermediate Similarity	NPC473491
0.7427	Intermediate Similarity	NPC168861
0.7423	Intermediate Similarity	NPC227953
0.7423	Intermediate Similarity	NPC302715
0.7409	Intermediate Similarity	NPC248822
0.738	Intermediate Similarity	NPC473546
0.7358	Intermediate Similarity	NPC61332
0.7358	Intermediate Similarity	NPC240130
0.7356	Intermediate Similarity	NPC16188
0.7333	Intermediate Similarity	NPC244336
0.7326	Intermediate Similarity	NPC196243
0.7293	Intermediate Similarity	NPC469243
0.7293	Intermediate Similarity	NPC475544
0.7292	Intermediate Similarity	NPC77435
0.7292	Intermediate Similarity	NPC259071
0.7282	Intermediate Similarity	NPC477631
0.7273	Intermediate Similarity	NPC477552
0.7273	Intermediate Similarity	NPC477550
0.7268	Intermediate Similarity	NPC477636
0.7267	Intermediate Similarity	NPC476989
0.7263	Intermediate Similarity	NPC473580
0.7263	Intermediate Similarity	NPC244509
0.7259	Intermediate Similarity	NPC329295
0.7258	Intermediate Similarity	NPC328494
0.7257	Intermediate Similarity	NPC311658
0.7247	Intermediate Similarity	NPC56685
0.7247	Intermediate Similarity	NPC262166
0.7209	Intermediate Similarity	NPC197045
0.7204	Intermediate Similarity	NPC475123
0.7204	Intermediate Similarity	NPC475204
0.72	Intermediate Similarity	NPC477551
0.7189	Intermediate Similarity	NPC209463
0.7189	Intermediate Similarity	NPC328649
0.7188	Intermediate Similarity	NPC477254
0.7181	Intermediate Similarity	NPC26108
0.7174	Intermediate Similarity	NPC223207
0.7158	Intermediate Similarity	NPC241794
0.7151	Intermediate Similarity	NPC202198
0.7143	Intermediate Similarity	NPC50016
0.7135	Intermediate Similarity	NPC304074
0.7135	Intermediate Similarity	NPC471771
0.7135	Intermediate Similarity	NPC61004
0.7135	Intermediate Similarity	NPC290755
0.7128	Intermediate Similarity	NPC273755
0.7121	Intermediate Similarity	NPC202866
0.7121	Intermediate Similarity	NPC475843
0.712	Intermediate Similarity	NPC153554
0.7114	Intermediate Similarity	NPC471337
0.7114	Intermediate Similarity	NPC469443
0.711	Intermediate Similarity	NPC214988
0.7097	Intermediate Similarity	NPC302597
0.7088	Intermediate Similarity	NPC233926
0.7088	Intermediate Similarity	NPC323336
0.7088	Intermediate Similarity	NPC326349
0.7085	Intermediate Similarity	NPC477639
0.7071	Intermediate Similarity	NPC474678
0.7071	Intermediate Similarity	NPC471338
0.7059	Intermediate Similarity	NPC66490
0.7039	Intermediate Similarity	NPC20755
0.7037	Intermediate Similarity	NPC248670
0.7026	Intermediate Similarity	NPC8093
0.7026	Intermediate Similarity	NPC121571
0.7021	Intermediate Similarity	NPC46009
0.7011	Intermediate Similarity	NPC48202
0.7	Intermediate Similarity	NPC233702
0.7	Intermediate Similarity	NPC136797
0.6979	Remote Similarity	NPC45037
0.6977	Remote Similarity	NPC267237
0.6961	Remote Similarity	NPC261934
0.6961	Remote Similarity	NPC5194
0.6959	Remote Similarity	NPC473724
0.6957	Remote Similarity	NPC478005
0.6954	Remote Similarity	NPC313694
0.6954	Remote Similarity	NPC147847
0.6954	Remote Similarity	NPC242159
0.6947	Remote Similarity	NPC137627
0.6923	Remote Similarity	NPC47672
0.6911	Remote Similarity	NPC473354
0.6908	Remote Similarity	NPC220060
0.6907	Remote Similarity	NPC477637
0.6904	Remote Similarity	NPC174607
0.6901	Remote Similarity	NPC474087
0.6875	Remote Similarity	NPC469444
0.6865	Remote Similarity	NPC1390
0.6865	Remote Similarity	NPC62104
0.6862	Remote Similarity	NPC254700
0.6859	Remote Similarity	NPC306804
0.6854	Remote Similarity	NPC315266
0.6847	Remote Similarity	NPC33064
0.6842	Remote Similarity	NPC40234
0.6825	Remote Similarity	NPC107938
0.6825	Remote Similarity	NPC294516
0.6823	Remote Similarity	NPC476227
0.6816	Remote Similarity	NPC81026
0.6811	Remote Similarity	NPC156311
0.6791	Remote Similarity	NPC73655
0.6777	Remote Similarity	NPC469445
0.676	Remote Similarity	NPC266741
0.6753	Remote Similarity	NPC143450
0.6746	Remote Similarity	NPC219350
0.6746	Remote Similarity	NPC194699
0.6739	Remote Similarity	NPC469711
0.6738	Remote Similarity	NPC114806
0.6737	Remote Similarity	NPC141957
0.6735	Remote Similarity	NPC476321
0.6722	Remote Similarity	NPC470472
0.6721	Remote Similarity	NPC76412
0.672	Remote Similarity	NPC5719
0.672	Remote Similarity	NPC217804
0.672	Remote Similarity	NPC324850
0.672	Remote Similarity	NPC210377
0.672	Remote Similarity	NPC22883
0.6719	Remote Similarity	NPC477255
0.6719	Remote Similarity	NPC230611
0.6718	Remote Similarity	NPC194671
0.6718	Remote Similarity	NPC269750
0.6714	Remote Similarity	NPC470746
0.6714	Remote Similarity	NPC471336
0.6701	Remote Similarity	NPC471526
0.6684	Remote Similarity	NPC24617
0.6682	Remote Similarity	NPC478007
0.6682	Remote Similarity	NPC214142
0.6667	Remote Similarity	NPC294951
0.6667	Remote Similarity	NPC326966
0.6667	Remote Similarity	NPC475735
0.6667	Remote Similarity	NPC308571
0.6652	Remote Similarity	NPC261251
0.6649	Remote Similarity	NPC279871
0.6649	Remote Similarity	NPC63040
0.6649	Remote Similarity	NPC473402
0.6649	Remote Similarity	NPC155506
0.6649	Remote Similarity	NPC159767
0.6649	Remote Similarity	NPC158277
0.6649	Remote Similarity	NPC39431
0.663	Remote Similarity	NPC300443
0.6629	Remote Similarity	NPC470470
0.6622	Remote Similarity	NPC100547
0.6621	Remote Similarity	NPC478008
0.662	Remote Similarity	NPC469442
0.662	Remote Similarity	NPC277306
0.6618	Remote Similarity	NPC123140
0.6611	Remote Similarity	NPC326241
0.6609	Remote Similarity	NPC474091
0.6601	Remote Similarity	NPC102245
0.6601	Remote Similarity	NPC64066
0.6597	Remote Similarity	NPC15068
0.6596	Remote Similarity	NPC319320
0.6596	Remote Similarity	NPC287757
0.6595	Remote Similarity	NPC258222
0.6592	Remote Similarity	NPC223409
0.6592	Remote Similarity	NPC95240
0.6592	Remote Similarity	NPC322135
0.6588	Remote Similarity	NPC6975
0.6583	Remote Similarity	NPC471049
0.6583	Remote Similarity	NPC471050
0.6583	Remote Similarity	NPC471048
0.6579	Remote Similarity	NPC133470
0.6579	Remote Similarity	NPC191863
0.6579	Remote Similarity	NPC289776
0.6577	Remote Similarity	NPC304307
0.6577	Remote Similarity	NPC118559
0.6577	Remote Similarity	NPC124920
0.6577	Remote Similarity	NPC34580
0.6569	Remote Similarity	NPC473941
0.6562	Remote Similarity	NPC14288
0.6558	Remote Similarity	NPC25539
0.6556	Remote Similarity	NPC251439
0.655	Remote Similarity	NPC299806

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 NPC246591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	461
0.2-0.3	826
0.3-0.4	2438
0.4-0.5	3981
0.5-0.6	1228
0.6-0.7	60
0.7-0.8	4
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
0.7709	Intermediate Similarity	NPD8303	Discontinued
0.7374	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7495	Discontinued
0.7181	Intermediate Similarity	NPD5200	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7523	Phase 3
0.702	Intermediate Similarity	NPD5165	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7617	Discontinued
0.6984	Remote Similarity	NPD5137	Approved
0.6957	Remote Similarity	NPD8019	Approved
0.6816	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7303	Discontinued
0.6705	Remote Similarity	NPD9718	Approved
0.6702	Remote Similarity	NPD7485	Phase 3
0.6702	Remote Similarity	NPD7484	Phase 3
0.6667	Remote Similarity	NPD4652	Approved
0.6648	Remote Similarity	NPD8076	Discontinued
0.6648	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3136	Phase 2
0.6592	Remote Similarity	NPD7450	Phase 2
0.6576	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6901	Phase 3
0.6571	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2098	Approved
0.6541	Remote Similarity	NPD7613	Discontinued
0.6538	Remote Similarity	NPD6676	Phase 2
0.6532	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD7978	Discontinued
0.6444	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.644	Remote Similarity	NPD2097	Approved
0.6417	Remote Similarity	NPD7131	Phase 3
0.6416	Remote Similarity	NPD8106	Phase 2
0.6398	Remote Similarity	NPD6419	Discontinued
0.6393	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6681	Discovery
0.6333	Remote Similarity	NPD6073	Approved
0.6333	Remote Similarity	NPD8173	Phase 2
0.6333	Remote Similarity	NPD8172	Phase 2
0.6305	Remote Similarity	NPD6557	Phase 2
0.6301	Remote Similarity	NPD2561	Approved
0.6301	Remote Similarity	NPD2562	Approved
0.6292	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD1330	Phase 2
0.6289	Remote Similarity	NPD4521	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD5263	Approved
0.6264	Remote Similarity	NPD6867	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD6866	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7608	Discontinued
0.6243	Remote Similarity	NPD5314	Approved
0.6209	Remote Similarity	NPD3552	Approved
0.6209	Remote Similarity	NPD3553	Approved
0.6209	Remote Similarity	NPD3554	Approved
0.6209	Remote Similarity	NPD3555	Approved
0.6193	Remote Similarity	NPD2017	Approved
0.6193	Remote Similarity	NPD2889	Approved
0.6193	Remote Similarity	NPD2890	Approved
0.6193	Remote Similarity	NPD2888	Approved
0.6188	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD1136	Approved
0.6167	Remote Similarity	NPD1132	Approved
0.6167	Remote Similarity	NPD1130	Approved
0.6158	Remote Similarity	NPD7451	Discontinued
0.6154	Remote Similarity	NPD2568	Approved
0.6141	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD3985	Discontinued
0.6135	Remote Similarity	NPD4157	Discontinued
0.6134	Remote Similarity	NPD5773	Approved
0.6134	Remote Similarity	NPD5772	Approved
0.6133	Remote Similarity	NPD3059	Approved
0.6133	Remote Similarity	NPD3061	Approved
0.6133	Remote Similarity	NPD3062	Approved
0.6122	Remote Similarity	NPD5219	Approved
0.6122	Remote Similarity	NPD5218	Approved
0.6122	Remote Similarity	NPD8031	Discontinued
0.6119	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD601	Approved
0.6111	Remote Similarity	NPD597	Approved
0.6111	Remote Similarity	NPD598	Approved
0.6105	Remote Similarity	NPD2183	Approved
0.6105	Remote Similarity	NPD2184	Approved
0.6103	Remote Similarity	NPD5967	Approved
0.6085	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD1423	Approved
0.607	Remote Similarity	NPD8292	Phase 2
0.6068	Remote Similarity	NPD6853	Approved
0.6068	Remote Similarity	NPD6851	Approved
0.6068	Remote Similarity	NPD6237	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD817	Approved
0.6066	Remote Similarity	NPD823	Approved
0.6066	Remote Similarity	NPD5725	Approved
0.6059	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD2874	Phase 2
0.6047	Remote Similarity	NPD856	Approved
0.6047	Remote Similarity	NPD317	Approved
0.6047	Remote Similarity	NPD16	Approved
0.6047	Remote Similarity	NPD318	Approved
0.6044	Remote Similarity	NPD4153	Approved
0.6043	Remote Similarity	NPD2211	Approved
0.6043	Remote Similarity	NPD2209	Approved
0.6041	Remote Similarity	NPD8070	Approved
0.6034	Remote Similarity	NPD7342	Discontinued
0.6034	Remote Similarity	NPD3040	Approved
0.6034	Remote Similarity	NPD4177	Approved
0.6034	Remote Similarity	NPD4847	Phase 1
0.6034	Remote Similarity	NPD4175	Approved
0.6031	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD6297	Approved
0.6023	Remote Similarity	NPD3071	Approved
0.6023	Remote Similarity	NPD3072	Approved
0.6023	Remote Similarity	NPD3073	Approved
0.6012	Remote Similarity	NPD2218	Phase 2
0.6012	Remote Similarity	NPD2217	Approved
0.6011	Remote Similarity	NPD3055	Approved
0.6011	Remote Similarity	NPD3053	Approved
0.601	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7011	Discontinued
0.6	Remote Similarity	NPD4676	Approved
0.6	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6796	Discontinued
0.5989	Remote Similarity	NPD4659	Approved
0.5979	Remote Similarity	NPD8323	Discontinued
0.5979	Remote Similarity	NPD8417	Discontinued
0.5979	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD2978	Approved
0.5969	Remote Similarity	NPD2977	Approved
0.5969	Remote Similarity	NPD3645	Discontinued
0.5969	Remote Similarity	NPD3536	Discontinued
0.5968	Remote Similarity	NPD2240	Approved
0.5968	Remote Similarity	NPD2239	Approved
0.5966	Remote Similarity	NPD4762	Approved
0.5966	Remote Similarity	NPD4761	Approved
0.5957	Remote Similarity	NPD3638	Discontinued
0.5956	Remote Similarity	NPD5323	Approved
0.5956	Remote Similarity	NPD6346	Approved
0.5955	Remote Similarity	NPD5310	Approved
0.5955	Remote Similarity	NPD3125	Approved
0.5955	Remote Similarity	NPD5311	Approved
0.5946	Remote Similarity	NPD6852	Discontinued
0.5945	Remote Similarity	NPD8162	Phase 2
0.5945	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD6863	Phase 2
0.5939	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7282	Approved
0.5931	Remote Similarity	NPD6042	Phase 2
0.5931	Remote Similarity	NPD42	Phase 2
0.5929	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD3592	Approved
0.5928	Remote Similarity	NPD3591	Approved
0.5924	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4103	Phase 2
0.5922	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.592	Remote Similarity	NPD316	Approved
0.5918	Remote Similarity	NPD4227	Discontinued
0.5913	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD8025	Phase 2
0.5905	Remote Similarity	NPD6835	Approved
0.5902	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6407	Approved
0.5902	Remote Similarity	NPD6405	Approved
0.5899	Remote Similarity	NPD6256	Approved
0.5899	Remote Similarity	NPD6254	Approved
0.5899	Remote Similarity	NPD6255	Approved
0.5897	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD3123	Discovery
0.5893	Remote Similarity	NPD6189	Approved
0.5893	Remote Similarity	NPD6188	Approved
0.5892	Remote Similarity	NPD3052	Approved
0.5892	Remote Similarity	NPD3054	Approved
0.5889	Remote Similarity	NPD9619	Approved
0.5889	Remote Similarity	NPD599	Approved
0.5889	Remote Similarity	NPD602	Approved
0.5889	Remote Similarity	NPD9621	Approved
0.5889	Remote Similarity	NPD9620	Approved
0.5882	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.588	Remote Similarity	NPD7810	Phase 3
0.588	Remote Similarity	NPD7811	Phase 3
0.5877	Remote Similarity	NPD6836	Approved
0.5873	Remote Similarity	NPD3060	Approved
0.5873	Remote Similarity	NPD2459	Approved
0.5873	Remote Similarity	NPD2460	Phase 3
0.5873	Remote Similarity	NPD2458	Approved
0.5873	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.587	Remote Similarity	NPD8416	Discontinued
0.5867	Remote Similarity	NPD6677	Suspended
0.5867	Remote Similarity	NPD2469	Approved
0.5867	Remote Similarity	NPD2468	Approved
0.5865	Remote Similarity	NPD7281	Phase 3

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