NPASS Compound

Structure

NPC203426 OpenBabel07101718312D 52 59 0 0 1 0 0 0 0 0999 V2000 7.4782 -3.2009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5711 -5.9652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7349 -3.8699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8381 -5.2850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7839 -3.5606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0606 -4.3101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6252 -2.2732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2387 -3.0404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5762 -2.5824 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0162 -4.0153 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4176 -1.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5056 -2.3602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4666 -0.9857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7233 -1.6547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2589 -0.0075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7723 -1.3454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3079 0.3017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5646 -0.3672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3196 1.0725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0147 0.1029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6202 1.2575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0395 0.8260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0022 0.6614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0688 -1.5307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9295 1.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4613 -0.3692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1609 -0.6260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8183 -2.6300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0953 2.2216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0010 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6783 1.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4854 -1.0962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6256 1.8539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4636 0.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9532 0.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1789 -2.2608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6756 2.0836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1118 -0.9353 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.7436 -3.6272 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.8816 3.1985 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8992 1.0263 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 6.3195 -1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7492 -4.6955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3136 2.1332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4007 -1.5597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7286 2.2960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2428 1.9338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6965 1.0211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3527 -2.8241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3062 2.8597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9017 -0.4323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 9 1 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 12 1 0 0 0 0 9 43 1 6 0 0 0 10 44 1 6 0 0 0 11 13 2 0 0 0 0 11 27 1 0 0 0 0 12 14 2 0 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 23 2 0 0 0 0 16 18 1 0 0 0 0 16 24 2 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 31 1 0 0 0 0 23 35 1 0 0 0 0 24 32 1 0 0 0 0 24 36 1 0 0 0 0 25 31 1 0 0 0 0 25 37 2 0 0 0 0 26 32 1 0 0 0 0 26 38 2 0 0 0 0 27 35 2 0 0 0 0 27 39 1 0 0 0 0 28 36 2 0 0 0 0 28 40 1 0 0 0 0 29 33 2 0 0 0 0 29 37 1 0 0 0 0 29 41 1 0 0 0 0 30 34 2 0 0 0 0 30 38 1 0 0 0 0 30 42 1 0 0 0 0 31 45 2 0 0 0 0 32 46 2 0 0 0 0 33 47 1 0 0 0 0 34 48 1 0 0 0 0 35 49 1 0 0 0 0 36 50 1 0 0 0 0 37 51 1 0 0 0 0 38 52 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	959.84
Volume:	722.842
LogP:	9.062
LogD:	2.166
LogS:	-6.748
# Rotatable Bonds:	8
TPSA:	195.98
# H-Bond Aceptor:	10
# H-Bond Donor:	8
# Rings:	8
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.054
Synthetic Accessibility Score:	4.75
Fsp3:	0.263
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.703
MDCK Permeability:	1.4661832210549619e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.995
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	105.2134017944336%
Volume Distribution (VD):	0.416
Pgp-substrate:	2.4942240715026855%

ADMET: Metabolism

CYP1A2-inhibitor:	0.282
CYP1A2-substrate:	0.172
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.482
CYP2C9-substrate:	0.642
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.001
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	-0.156
Half-life (T1/2):	0.124

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.273
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.931
Carcinogencity:	0.15
Eye Corrosion:	0.003
Eye Irritation:	0.812
Respiratory Toxicity:	0.042

Download Data

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

Natural Product: NPC203426

Natural Product ID:	NPC203426
*Common Name:**	Gymnochrome F
IUPAC Name:	n.a.
Synonyms:	Gymnochrome F
Standard InCHIKey:	VXMCGKZBNQKQJM-NXEZZACHSA-N
Standard InCHI:	InChI=1S/C38H28Br4O10/c1-3-5-9(43)7-11-13-14-12(8-10(44)6-4-2)28(40)36(50)24-16(14)18-17-15(13)23(35(49)27(11)39)31(45)25-19(17)21(33(47)29(41)37(25)51)22-20(18)26(32(24)46)38(52)30(42)34(22)48/h9-10,43-44,47-52H,3-8H2,1-2H3/t9-,10-/m1/s1
SMILES:	CCC[C@H](Cc1c2c3c(C[C@@H](CCC)O)c(c(c4c3c3c5c2c(C(=O)c2c5c(c5c3c(C4=O)c(c(c5O)Br)O)c(c(c2O)Br)O)c(c1Br)O)O)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094578
PubChem CID:	15101872
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0001851] Pyrenes [CHEMONTID:0000316] Benzopyrenes

*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
NPO13709	Holopus rangii	Species	Holopodidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20158243]
NPO13709	Holopus rangii	Species	Holopodidae	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
IC50	1
MIC	2

Activity Type	# Activity
Individual Protein	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT57	Individual Protein	Induced myeloid leukemia cell differentiation protein Mcl-1	Homo sapiens	IC50	=	3300.0	nM	PMID[507400]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	12.5	ug.mL-1	PMID[507400]

☑ 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 NPC203426 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	463
0.1-0.2	2153
0.2-0.3	5469
0.3-0.4	13578
0.4-0.5	7442
0.5-0.6	7056
0.6-0.7	6195
0.7-0.8	333
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9625	High Similarity	NPC24435
0.8333	Intermediate Similarity	NPC477221
0.8323	Intermediate Similarity	NPC290194
0.8198	Intermediate Similarity	NPC470567
0.814	Intermediate Similarity	NPC470566
0.8137	Intermediate Similarity	NPC227841
0.7988	Intermediate Similarity	NPC37709
0.7963	Intermediate Similarity	NPC293545
0.7963	Intermediate Similarity	NPC174905
0.7853	Intermediate Similarity	NPC451542
0.7853	Intermediate Similarity	NPC313047
0.7853	Intermediate Similarity	NPC295712
0.7853	Intermediate Similarity	NPC474203
0.7853	Intermediate Similarity	NPC296752
0.7791	Intermediate Similarity	NPC474961
0.7758	Intermediate Similarity	NPC12402
0.7714	Intermediate Similarity	NPC469664
0.7697	Intermediate Similarity	NPC10764
0.7688	Intermediate Similarity	NPC472052
0.7688	Intermediate Similarity	NPC470342
0.7688	Intermediate Similarity	NPC472060
0.7683	Intermediate Similarity	NPC135524
0.7683	Intermediate Similarity	NPC85310
0.7622	Intermediate Similarity	NPC305845
0.7622	Intermediate Similarity	NPC246638
0.7622	Intermediate Similarity	NPC204045
0.7605	Intermediate Similarity	NPC110882
0.7605	Intermediate Similarity	NPC85393
0.7605	Intermediate Similarity	NPC271944
0.76	Intermediate Similarity	NPC15374
0.759	Intermediate Similarity	NPC244691
0.759	Intermediate Similarity	NPC471906
0.7588	Intermediate Similarity	NPC35
0.7576	Intermediate Similarity	NPC19631
0.7576	Intermediate Similarity	NPC239136
0.7543	Intermediate Similarity	NPC273467
0.7543	Intermediate Similarity	NPC189552
0.7531	Intermediate Similarity	NPC191976
0.753	Intermediate Similarity	NPC471682
0.7529	Intermediate Similarity	NPC324736
0.7528	Intermediate Similarity	NPC470341
0.7528	Intermediate Similarity	NPC472058
0.7528	Intermediate Similarity	NPC234497
0.7528	Intermediate Similarity	NPC105414
0.7528	Intermediate Similarity	NPC324522
0.7514	Intermediate Similarity	NPC477991
0.7514	Intermediate Similarity	NPC477992
0.75	Intermediate Similarity	NPC477836
0.75	Intermediate Similarity	NPC190457
0.75	Intermediate Similarity	NPC472211
0.7486	Intermediate Similarity	NPC186325
0.7486	Intermediate Similarity	NPC312993
0.7485	Intermediate Similarity	NPC474110
0.7485	Intermediate Similarity	NPC84426
0.7485	Intermediate Similarity	NPC44960
0.7472	Intermediate Similarity	NPC477835
0.747	Intermediate Similarity	NPC257644
0.747	Intermediate Similarity	NPC469520
0.7458	Intermediate Similarity	NPC471687
0.7453	Intermediate Similarity	NPC267205
0.7443	Intermediate Similarity	NPC18380
0.744	Intermediate Similarity	NPC471683
0.744	Intermediate Similarity	NPC34482
0.7429	Intermediate Similarity	NPC177650
0.7427	Intermediate Similarity	NPC477914
0.7401	Intermediate Similarity	NPC315772
0.7396	Intermediate Similarity	NPC143685
0.7396	Intermediate Similarity	NPC470570
0.7394	Intermediate Similarity	NPC242994
0.7394	Intermediate Similarity	NPC138099
0.7386	Intermediate Similarity	NPC292863
0.7386	Intermediate Similarity	NPC184326
0.7381	Intermediate Similarity	NPC160839
0.7381	Intermediate Similarity	NPC48762
0.7378	Intermediate Similarity	NPC471905
0.7374	Intermediate Similarity	NPC293312
0.7365	Intermediate Similarity	NPC137649
0.736	Intermediate Similarity	NPC290160
0.7356	Intermediate Similarity	NPC66508
0.7356	Intermediate Similarity	NPC266469
0.7356	Intermediate Similarity	NPC226656
0.7349	Intermediate Similarity	NPC181560
0.7349	Intermediate Similarity	NPC169452
0.7346	Intermediate Similarity	NPC314048
0.7345	Intermediate Similarity	NPC472261
0.7345	Intermediate Similarity	NPC137232
0.7342	Intermediate Similarity	NPC472047
0.7333	Intermediate Similarity	NPC87723
0.733	Intermediate Similarity	NPC228654
0.733	Intermediate Similarity	NPC195167
0.733	Intermediate Similarity	NPC51760
0.733	Intermediate Similarity	NPC18699
0.733	Intermediate Similarity	NPC55443
0.7318	Intermediate Similarity	NPC472051
0.7318	Intermediate Similarity	NPC472057
0.7317	Intermediate Similarity	NPC254847
0.7305	Intermediate Similarity	NPC106519
0.7305	Intermediate Similarity	NPC92079
0.7305	Intermediate Similarity	NPC110810
0.7305	Intermediate Similarity	NPC91019
0.7303	Intermediate Similarity	NPC472059
0.7301	Intermediate Similarity	NPC474224
0.7301	Intermediate Similarity	NPC474117
0.7301	Intermediate Similarity	NPC472262
0.7301	Intermediate Similarity	NPC287604
0.7301	Intermediate Similarity	NPC161964
0.7299	Intermediate Similarity	NPC218870
0.7299	Intermediate Similarity	NPC474824
0.7299	Intermediate Similarity	NPC182921
0.7299	Intermediate Similarity	NPC470408
0.7294	Intermediate Similarity	NPC472134
0.7294	Intermediate Similarity	NPC314437
0.7293	Intermediate Similarity	NPC264063
0.7293	Intermediate Similarity	NPC469486
0.729	Intermediate Similarity	NPC229649
0.7289	Intermediate Similarity	NPC143438
0.7283	Intermediate Similarity	NPC470569
0.7278	Intermediate Similarity	NPC21599
0.7278	Intermediate Similarity	NPC477913
0.7278	Intermediate Similarity	NPC193703
0.7273	Intermediate Similarity	NPC53414
0.7273	Intermediate Similarity	NPC208258
0.7273	Intermediate Similarity	NPC53206
0.7273	Intermediate Similarity	NPC53001
0.7273	Intermediate Similarity	NPC62272
0.7268	Intermediate Similarity	NPC470333
0.7263	Intermediate Similarity	NPC472053
0.7262	Intermediate Similarity	NPC193555
0.7257	Intermediate Similarity	NPC318270
0.7257	Intermediate Similarity	NPC66029
0.7251	Intermediate Similarity	NPC34802
0.7247	Intermediate Similarity	NPC219686
0.7247	Intermediate Similarity	NPC312273
0.7247	Intermediate Similarity	NPC301256
0.7241	Intermediate Similarity	NPC43345
0.7239	Intermediate Similarity	NPC114183
0.7239	Intermediate Similarity	NPC139074
0.7239	Intermediate Similarity	NPC213485
0.7239	Intermediate Similarity	NPC40524
0.7235	Intermediate Similarity	NPC68441
0.7235	Intermediate Similarity	NPC88896
0.7235	Intermediate Similarity	NPC170055
0.7225	Intermediate Similarity	NPC205766
0.7225	Intermediate Similarity	NPC280295
0.7225	Intermediate Similarity	NPC470568
0.7225	Intermediate Similarity	NPC147735
0.7222	Intermediate Similarity	NPC72669
0.7222	Intermediate Similarity	NPC474517
0.7219	Intermediate Similarity	NPC473631
0.7219	Intermediate Similarity	NPC475662
0.7219	Intermediate Similarity	NPC473717
0.7219	Intermediate Similarity	NPC293227
0.7216	Intermediate Similarity	NPC474861
0.7212	Intermediate Similarity	NPC472599
0.7212	Intermediate Similarity	NPC118919
0.7209	Intermediate Similarity	NPC221352
0.7209	Intermediate Similarity	NPC142846
0.7207	Intermediate Similarity	NPC473012
0.7202	Intermediate Similarity	NPC187843
0.7198	Intermediate Similarity	NPC300307
0.7197	Intermediate Similarity	NPC232708
0.7195	Intermediate Similarity	NPC166480
0.7195	Intermediate Similarity	NPC270899
0.7195	Intermediate Similarity	NPC12070
0.7195	Intermediate Similarity	NPC282780
0.7193	Intermediate Similarity	NPC285122
0.7191	Intermediate Similarity	NPC476506
0.7184	Intermediate Similarity	NPC476553
0.7184	Intermediate Similarity	NPC149526
0.7184	Intermediate Similarity	NPC474417
0.7184	Intermediate Similarity	NPC476552
0.7184	Intermediate Similarity	NPC476551
0.7184	Intermediate Similarity	NPC232645
0.7184	Intermediate Similarity	NPC72958
0.7182	Intermediate Similarity	NPC251336
0.7176	Intermediate Similarity	NPC84568
0.7176	Intermediate Similarity	NPC48130
0.7176	Intermediate Similarity	NPC300684
0.7176	Intermediate Similarity	NPC218866
0.7175	Intermediate Similarity	NPC317580
0.7175	Intermediate Similarity	NPC257166
0.7175	Intermediate Similarity	NPC475184
0.7174	Intermediate Similarity	NPC131862
0.7174	Intermediate Similarity	NPC470336
0.7174	Intermediate Similarity	NPC470335
0.7174	Intermediate Similarity	NPC229051
0.7168	Intermediate Similarity	NPC329933
0.7167	Intermediate Similarity	NPC473009
0.716	Intermediate Similarity	NPC476508
0.716	Intermediate Similarity	NPC147757
0.716	Intermediate Similarity	NPC73061
0.7159	Intermediate Similarity	NPC52611
0.7159	Intermediate Similarity	NPC159707
0.7159	Intermediate Similarity	NPC100049
0.7159	Intermediate Similarity	NPC265624
0.7159	Intermediate Similarity	NPC186227
0.7159	Intermediate Similarity	NPC215203
0.7159	Intermediate Similarity	NPC254351
0.7159	Intermediate Similarity	NPC37253
0.7159	Intermediate Similarity	NPC121649

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 NPC203426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	1269
0.2-0.3	2442
0.3-0.4	3168
0.4-0.5	1363
0.5-0.6	387
0.6-0.7	98
0.7-0.8	4
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
0.8137	Intermediate Similarity	NPD7390	Discontinued
0.7644	Intermediate Similarity	NPD6959	Discontinued
0.7317	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD5405	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7235	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4287	Approved
0.6923	Remote Similarity	NPD6232	Discontinued
0.6902	Remote Similarity	NPD7473	Discontinued
0.6872	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2533	Approved
0.6839	Remote Similarity	NPD2534	Approved
0.6839	Remote Similarity	NPD2532	Approved
0.6742	Remote Similarity	NPD4380	Phase 2
0.6722	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6166	Phase 2
0.6649	Remote Similarity	NPD5844	Phase 1
0.6649	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7768	Phase 2
0.663	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1201	Approved
0.6593	Remote Similarity	NPD4288	Approved
0.6588	Remote Similarity	NPD6651	Approved
0.6585	Remote Similarity	NPD8151	Discontinued
0.6582	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8312	Approved
0.6562	Remote Similarity	NPD8313	Approved
0.6554	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1470	Approved
0.6519	Remote Similarity	NPD7411	Suspended
0.6503	Remote Similarity	NPD2296	Approved
0.6474	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD943	Approved
0.6462	Remote Similarity	NPD8150	Discontinued
0.6458	Remote Similarity	NPD6559	Discontinued
0.6432	Remote Similarity	NPD6535	Approved
0.6432	Remote Similarity	NPD6534	Approved
0.6418	Remote Similarity	NPD7699	Phase 2
0.6418	Remote Similarity	NPD7700	Phase 2
0.6416	Remote Similarity	NPD1510	Phase 2
0.6406	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1607	Approved
0.6393	Remote Similarity	NPD1934	Approved
0.639	Remote Similarity	NPD7871	Phase 2
0.639	Remote Similarity	NPD7870	Phase 2
0.6383	Remote Similarity	NPD5710	Approved
0.6383	Remote Similarity	NPD5711	Approved
0.6364	Remote Similarity	NPD2800	Approved
0.6354	Remote Similarity	NPD7074	Phase 3
0.6344	Remote Similarity	NPD3749	Approved
0.6344	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7075	Discontinued
0.6343	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7003	Approved
0.6322	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD1549	Phase 2
0.6307	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6801	Discontinued
0.6302	Remote Similarity	NPD7054	Approved
0.629	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD1240	Approved
0.6275	Remote Similarity	NPD6782	Approved
0.6275	Remote Similarity	NPD6776	Approved
0.6275	Remote Similarity	NPD6779	Approved
0.6275	Remote Similarity	NPD6777	Approved
0.6275	Remote Similarity	NPD6778	Approved
0.6275	Remote Similarity	NPD6781	Approved
0.6275	Remote Similarity	NPD6780	Approved
0.6269	Remote Similarity	NPD7472	Approved
0.6262	Remote Similarity	NPD7698	Approved
0.6262	Remote Similarity	NPD7697	Approved
0.6262	Remote Similarity	NPD7696	Phase 3
0.6256	Remote Similarity	NPD7808	Phase 3
0.6237	Remote Similarity	NPD6797	Phase 2
0.6232	Remote Similarity	NPD8319	Approved
0.6232	Remote Similarity	NPD8320	Phase 1
0.623	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.623	Remote Similarity	NPD3226	Approved
0.6219	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD6213	Phase 3
0.6219	Remote Similarity	NPD6212	Phase 3
0.6205	Remote Similarity	NPD7251	Discontinued
0.6193	Remote Similarity	NPD2935	Discontinued
0.6193	Remote Similarity	NPD2796	Approved
0.619	Remote Similarity	NPD5494	Approved
0.6184	Remote Similarity	NPD7435	Discontinued
0.6183	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD2801	Approved
0.6166	Remote Similarity	NPD3818	Discontinued
0.6143	Remote Similarity	NPD7701	Phase 2
0.6141	Remote Similarity	NPD7458	Discontinued
0.6133	Remote Similarity	NPD1511	Approved
0.6132	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7783	Phase 2
0.6085	Remote Similarity	NPD7874	Approved
0.6085	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD3300	Phase 2
0.6067	Remote Similarity	NPD2346	Discontinued
0.6066	Remote Similarity	NPD1512	Approved
0.6064	Remote Similarity	NPD3817	Phase 2
0.6064	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD1164	Approved
0.6058	Remote Similarity	NPD6823	Phase 2
0.6056	Remote Similarity	NPD3750	Approved
0.6056	Remote Similarity	NPD7801	Approved
0.6048	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD37	Approved
0.6032	Remote Similarity	NPD3882	Suspended
0.6022	Remote Similarity	NPD6599	Discontinued
0.6011	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD1465	Phase 2
0.601	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7177	Discontinued
0.6	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD5402	Approved
0.5969	Remote Similarity	NPD6020	Phase 2
0.5967	Remote Similarity	NPD8166	Discontinued
0.5959	Remote Similarity	NPD3787	Discontinued
0.5955	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD7539	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD4966	Approved
0.5947	Remote Similarity	NPD4967	Phase 2
0.5947	Remote Similarity	NPD4965	Approved
0.5938	Remote Similarity	NPD7654	Discontinued
0.5931	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.593	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD8455	Phase 2
0.5922	Remote Similarity	NPD6100	Approved
0.5922	Remote Similarity	NPD6099	Approved
0.5918	Remote Similarity	NPD3751	Discontinued
0.5918	Remote Similarity	NPD7228	Approved
0.5894	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD3019	Approved
0.5886	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD6234	Discontinued
0.5879	Remote Similarity	NPD3400	Discontinued
0.5876	Remote Similarity	NPD7229	Phase 3
0.5874	Remote Similarity	NPD4360	Phase 2
0.5874	Remote Similarity	NPD4363	Phase 3
0.587	Remote Similarity	NPD6799	Approved
0.5869	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.5866	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.586	Remote Similarity	NPD920	Approved
0.586	Remote Similarity	NPD5403	Approved
0.585	Remote Similarity	NPD36	Approved
0.585	Remote Similarity	NPD5026	Approved
0.585	Remote Similarity	NPD5034	Approved
0.585	Remote Similarity	NPD4955	Approved
0.585	Remote Similarity	NPD4954	Approved
0.585	Remote Similarity	NPD5028	Approved
0.5843	Remote Similarity	NPD405	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1551	Phase 2
0.5829	Remote Similarity	NPD7008	Discontinued
0.5829	Remote Similarity	NPD5953	Discontinued
0.5821	Remote Similarity	NPD5035	Approved
0.5813	Remote Similarity	NPD5038	Approved
0.5813	Remote Similarity	NPD5037	Approved
0.581	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD7286	Phase 2
0.5806	Remote Similarity	NPD6273	Approved
0.5801	Remote Similarity	NPD2344	Approved
0.58	Remote Similarity	NPD5030	Phase 2
0.5799	Remote Similarity	NPD2932	Approved
0.5795	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD3764	Approved
0.5792	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD4628	Phase 3
0.5787	Remote Similarity	NPD230	Phase 1
0.5778	Remote Similarity	NPD3748	Approved
0.5776	Remote Similarity	NPD2342	Discontinued
0.5775	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD3926	Phase 2
0.5764	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD5036	Approved
0.5761	Remote Similarity	NPD6190	Approved
0.5758	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD5401	Approved
0.5744	Remote Similarity	NPD7199	Phase 2
0.5739	Remote Similarity	NPD4625	Phase 3
0.5738	Remote Similarity	NPD1243	Approved
0.5721	Remote Similarity	NPD5039	Approved
0.5707	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD4750	Phase 3
0.57	Remote Similarity	NPD4956	Approved
0.5698	Remote Similarity	NPD9269	Phase 2
0.5697	Remote Similarity	NPD7635	Approved
0.5693	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD2799	Discontinued
0.569	Remote Similarity	NPD3094	Phase 2
0.5687	Remote Similarity	NPD8285	Discontinued
0.5683	Remote Similarity	NPD8059	Phase 3
0.5683	Remote Similarity	NPD8058	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