NPASS Compound

Structure

NPC471403 OpenBabel07101719142D 60 70 0 0 1 0 0 0 0 0999 V2000 -5.7098 -0.7255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8704 0.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6629 -4.2309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8633 -3.5313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7404 1.3120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4480 2.3835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5492 -0.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7098 1.2131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2590 -5.1120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2672 -4.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3591 2.0582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0666 3.1297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1276 -0.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4921 -1.4140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1915 -2.1795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6732 -1.6948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9079 -1.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8704 -0.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1018 -3.4406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7849 1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5492 0.7284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7060 -5.2028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0222 2.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5779 -0.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3520 -1.6948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5126 -2.1795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5915 -0.6958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9637 -0.4209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0309 -1.6948 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9560 -1.6244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6732 -0.7255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2347 -1.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5057 -1.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3463 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5126 -0.2409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6173 -1.0693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0558 -1.3934 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5126 0.7284 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0309 -0.7255 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3520 -0.7255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6732 -0.3242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1117 -2.1385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6732 1.2131 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5057 -2.5594 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1663 0.7284 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3887 1.2131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1099 -6.0840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6408 3.7133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4802 -0.4903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5126 -3.1488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9241 0.5129 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7103 0.4202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8704 -2.1795 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9850 -2.5591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6732 2.1824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1915 -0.2409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9560 -2.2003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1788 -2.2352 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1663 -0.2409 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 18 2 0 0 0 0 2 8 2 0 0 0 0 2 18 1 0 0 0 0 3 9 1 0 0 0 0 3 19 2 0 0 0 0 4 10 2 0 0 0 0 4 19 1 0 0 0 0 5 11 1 0 0 0 0 5 20 2 0 0 0 0 6 12 2 0 0 0 0 6 20 1 0 0 0 0 7 21 2 0 0 0 0 8 21 1 0 0 0 0 9 22 2 0 0 0 0 10 22 1 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 13 27 1 0 0 0 0 14 24 1 0 0 0 0 14 30 2 0 0 0 0 15 25 1 0 0 0 0 15 29 1 0 0 0 0 16 26 2 0 0 0 0 16 31 1 0 0 0 0 17 28 2 0 0 0 0 17 32 1 0 0 0 0 21 46 1 0 0 0 0 22 47 1 0 0 0 0 23 48 1 0 0 0 0 24 49 1 0 0 0 0 25 26 1 0 0 0 0 25 40 2 0 0 0 0 26 50 1 0 0 0 0 27 33 2 0 0 0 0 27 51 1 0 0 0 0 28 34 1 0 0 0 0 28 52 1 0 0 0 0 29 39 1 0 0 0 0 29 53 1 1 0 0 0 30 33 1 0 0 0 0 30 57 1 0 0 0 0 31 35 2 0 0 0 0 31 59 1 0 0 0 0 32 36 2 0 0 0 0 32 58 1 0 0 0 0 34 41 2 0 0 0 0 35 38 1 0 0 0 0 35 40 1 0 0 0 0 36 37 1 0 0 0 0 36 41 1 0 0 0 0 37 33 1 6 0 0 0 37 42 1 0 0 0 0 38 34 1 6 0 0 0 38 43 1 0 0 0 0 39 18 1 6 0 0 0 39 56 1 0 0 0 0 40 56 1 0 0 0 0 41 60 1 0 0 0 0 42 44 1 6 0 0 0 42 54 1 0 0 0 0 43 45 1 6 0 0 0 43 55 1 0 0 0 0 44 19 1 6 0 0 0 44 57 1 0 0 0 0 44 58 1 0 0 0 0 45 20 1 6 0 0 0 45 59 1 0 0 0 0 45 60 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	814.19
Volume:	777.152
LogP:	5.265
LogD:	2.986
LogS:	-2.134
# Rotatable Bonds:	3
TPSA:	248.45
# H-Bond Aceptor:	15
# H-Bond Donor:	10
# Rings:	11
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	6.483
Fsp3:	0.2
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:	-6.594
MDCK Permeability:	9.600083103578072e-06
Pgp-inhibitor:	0.126
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.291
20% Bioavailability (F20%):	0.112
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	88.53596496582031%
Volume Distribution (VD):	0.148
Pgp-substrate:	8.347434997558594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.996
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.224
CYP3A4-substrate:	0.912

ADMET: Excretion

Clearance (CL):	11.022
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.216
Rat Oral Acute Toxicity:	0.657
Maximum Recommended Daily Dose:	0.105
Skin Sensitization:	0.955
Carcinogencity:	0.716
Eye Corrosion:	0.003
Eye Irritation:	0.897
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC471403

Natural Product ID:	NPC471403
*Common Name:**	MMBACJOZVSORQJ-WQDCACQGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MMBACJOZVSORQJ-WQDCACQGSA-N
Standard InCHI:	InChI=1S/C45H34O15/c46-21-7-1-18(2-8-21)39-29(53)15-25-26(50)16-31-35(40(25)56-39)38-34-28(52)17-32-36(41(34)60-45(59-31,43(38)55)20-5-11-23(48)12-6-20)37-33-27(51)13-24(49)14-30(33)57-44(58-32,42(37)54)19-3-9-22(47)10-4-19/h1-14,16-17,29,37-39,42-43,46-55H,15H2/t29-,37+,38+,39+,42+,43+,44-,45+/m1/s1
SMILES:	Oc1ccc(cc1)[C@]12Oc3cc(O)c4c(c3[C@@H]([C@@H]2O)c2c(O1)c1c(cc2O)O[C@@]2([C@H]([C@H]1c1c(O)cc(cc1O2)O)O)c1ccc(cc1)O)O[C@H]([C@@H](C4)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431894
PubChem CID:	72703042
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO32897	spenceria ramalana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24131240]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT35	Others	n.a.		IC50	=	39800.0	nM	PMID[554191]

☑ 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 NPC471403 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	497
0.1-0.2	1650
0.2-0.3	4558
0.3-0.4	11221
0.4-0.5	7201
0.5-0.6	5148
0.6-0.7	7529
0.7-0.8	4293
0.8-0.85	439
0.85-0.9	124
0.9-0.95	17
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9724	High Similarity	NPC259707
0.965	High Similarity	NPC248053
0.965	High Similarity	NPC155564
0.965	High Similarity	NPC102280
0.9533	High Similarity	NPC159526
0.9533	High Similarity	NPC106601
0.9533	High Similarity	NPC205613
0.9533	High Similarity	NPC212614
0.9533	High Similarity	NPC471404
0.9533	High Similarity	NPC151474
0.9533	High Similarity	NPC86630
0.9467	High Similarity	NPC73517
0.9467	High Similarity	NPC4809
0.9467	High Similarity	NPC147743
0.9301	High Similarity	NPC100482
0.9301	High Similarity	NPC277331
0.9276	High Similarity	NPC185231
0.9267	High Similarity	NPC46335
0.9262	High Similarity	NPC134911
0.9262	High Similarity	NPC59692
0.9262	High Similarity	NPC272552
0.9262	High Similarity	NPC322899
0.9262	High Similarity	NPC469944
0.9262	High Similarity	NPC226108
0.9262	High Similarity	NPC46283
0.9262	High Similarity	NPC44192
0.9241	High Similarity	NPC475492
0.92	High Similarity	NPC224161
0.9133	High Similarity	NPC279406
0.9133	High Similarity	NPC226809
0.9073	High Similarity	NPC20050
0.9073	High Similarity	NPC306267
0.9007	High Similarity	NPC233467
0.898	High Similarity	NPC225445
0.8974	High Similarity	NPC12326
0.8958	High Similarity	NPC470308
0.8958	High Similarity	NPC470307
0.8926	High Similarity	NPC236202
0.8926	High Similarity	NPC18185
0.8926	High Similarity	NPC262911
0.8926	High Similarity	NPC294558
0.8926	High Similarity	NPC170103
0.8926	High Similarity	NPC204770
0.8926	High Similarity	NPC82917
0.8926	High Similarity	NPC70409
0.8926	High Similarity	NPC263940
0.8926	High Similarity	NPC58190
0.8926	High Similarity	NPC108811
0.8926	High Similarity	NPC202742
0.8912	High Similarity	NPC116922
0.8889	High Similarity	NPC471522
0.8874	High Similarity	NPC477612
0.8859	High Similarity	NPC96576
0.8851	High Similarity	NPC177597
0.8808	High Similarity	NPC211561
0.875	High Similarity	NPC476616
0.875	High Similarity	NPC476617
0.875	High Similarity	NPC476615
0.8742	High Similarity	NPC20757
0.8742	High Similarity	NPC227516
0.8726	High Similarity	NPC100936
0.8726	High Similarity	NPC1253
0.8716	High Similarity	NPC84207
0.8716	High Similarity	NPC5253
0.8716	High Similarity	NPC139976
0.8716	High Similarity	NPC49542
0.8716	High Similarity	NPC230718
0.8716	High Similarity	NPC472353
0.8716	High Similarity	NPC128337
0.8699	High Similarity	NPC262328
0.8699	High Similarity	NPC87777
0.8693	High Similarity	NPC473621
0.8684	High Similarity	NPC470208
0.8684	High Similarity	NPC295573
0.8675	High Similarity	NPC153182
0.8675	High Similarity	NPC174251
0.8671	High Similarity	NPC48880
0.8649	High Similarity	NPC108674
0.8639	High Similarity	NPC475836
0.8618	High Similarity	NPC280945
0.8609	High Similarity	NPC215678
0.8609	High Similarity	NPC274454
0.8609	High Similarity	NPC14468
0.86	High Similarity	NPC28440
0.86	High Similarity	NPC171932
0.8571	High Similarity	NPC9309
0.8562	High Similarity	NPC79957
0.8553	High Similarity	NPC15538
0.8553	High Similarity	NPC473480
0.8542	High Similarity	NPC103799
0.8537	High Similarity	NPC168789
0.8526	High Similarity	NPC157333
0.8523	High Similarity	NPC257095
0.8523	High Similarity	NPC273932
0.8523	High Similarity	NPC178054
0.8523	High Similarity	NPC89686
0.8497	Intermediate Similarity	NPC281549
0.8487	Intermediate Similarity	NPC74320
0.8487	Intermediate Similarity	NPC107120
0.8477	Intermediate Similarity	NPC138227
0.8477	Intermediate Similarity	NPC168579
0.8477	Intermediate Similarity	NPC76176
0.8477	Intermediate Similarity	NPC469313
0.8442	Intermediate Similarity	NPC321657
0.8442	Intermediate Similarity	NPC318373
0.8435	Intermediate Similarity	NPC125579
0.8431	Intermediate Similarity	NPC112819
0.8431	Intermediate Similarity	NPC133209
0.8431	Intermediate Similarity	NPC6702
0.8431	Intermediate Similarity	NPC111134
0.8425	Intermediate Similarity	NPC92805
0.8421	Intermediate Similarity	NPC181615
0.8421	Intermediate Similarity	NPC23807
0.8411	Intermediate Similarity	NPC37793
0.8403	Intermediate Similarity	NPC93962
0.84	Intermediate Similarity	NPC210192
0.84	Intermediate Similarity	NPC5155
0.8387	Intermediate Similarity	NPC205501
0.8387	Intermediate Similarity	NPC472710
0.8387	Intermediate Similarity	NPC118000
0.8387	Intermediate Similarity	NPC162976
0.8387	Intermediate Similarity	NPC472709
0.8378	Intermediate Similarity	NPC20829
0.8378	Intermediate Similarity	NPC40664
0.8378	Intermediate Similarity	NPC262585
0.8378	Intermediate Similarity	NPC3293
0.8378	Intermediate Similarity	NPC197723
0.8378	Intermediate Similarity	NPC138350
0.8378	Intermediate Similarity	NPC18189
0.8378	Intermediate Similarity	NPC165482
0.8377	Intermediate Similarity	NPC270751
0.8367	Intermediate Similarity	NPC188555
0.8367	Intermediate Similarity	NPC124085
0.8367	Intermediate Similarity	NPC130496
0.8367	Intermediate Similarity	NPC184269
0.8367	Intermediate Similarity	NPC117048
0.8366	Intermediate Similarity	NPC125755
0.8366	Intermediate Similarity	NPC260397
0.8355	Intermediate Similarity	NPC151704
0.8354	Intermediate Similarity	NPC202104
0.8343	Intermediate Similarity	NPC321916
0.8333	Intermediate Similarity	NPC329343
0.8333	Intermediate Similarity	NPC53986
0.8333	Intermediate Similarity	NPC262189
0.8333	Intermediate Similarity	NPC274717
0.8333	Intermediate Similarity	NPC324517
0.8333	Intermediate Similarity	NPC38664
0.8333	Intermediate Similarity	NPC321972
0.8323	Intermediate Similarity	NPC122980
0.8323	Intermediate Similarity	NPC148516
0.8323	Intermediate Similarity	NPC177172
0.8323	Intermediate Similarity	NPC476969
0.8323	Intermediate Similarity	NPC107862
0.8323	Intermediate Similarity	NPC180605
0.8322	Intermediate Similarity	NPC474687
0.8311	Intermediate Similarity	NPC238243
0.8301	Intermediate Similarity	NPC277867
0.8301	Intermediate Similarity	NPC475096
0.8301	Intermediate Similarity	NPC149633
0.8301	Intermediate Similarity	NPC161700
0.8301	Intermediate Similarity	NPC271076
0.8299	Intermediate Similarity	NPC85435
0.8299	Intermediate Similarity	NPC77196
0.8299	Intermediate Similarity	NPC215037
0.8294	Intermediate Similarity	NPC318119
0.8288	Intermediate Similarity	NPC211413
0.8288	Intermediate Similarity	NPC164804
0.8288	Intermediate Similarity	NPC129784
0.8288	Intermediate Similarity	NPC280653
0.8288	Intermediate Similarity	NPC244888
0.8288	Intermediate Similarity	NPC236014
0.8288	Intermediate Similarity	NPC300875
0.8288	Intermediate Similarity	NPC207892
0.8288	Intermediate Similarity	NPC118683
0.8288	Intermediate Similarity	NPC12875
0.8288	Intermediate Similarity	NPC228369
0.8288	Intermediate Similarity	NPC129106
0.8288	Intermediate Similarity	NPC476166
0.8288	Intermediate Similarity	NPC268917
0.8288	Intermediate Similarity	NPC271945
0.8288	Intermediate Similarity	NPC118114
0.8288	Intermediate Similarity	NPC17343
0.8288	Intermediate Similarity	NPC196765
0.8288	Intermediate Similarity	NPC206224
0.8288	Intermediate Similarity	NPC164574
0.8288	Intermediate Similarity	NPC181497
0.8288	Intermediate Similarity	NPC293203
0.8288	Intermediate Similarity	NPC150011
0.8288	Intermediate Similarity	NPC68205
0.828	Intermediate Similarity	NPC21902
0.828	Intermediate Similarity	NPC120633
0.828	Intermediate Similarity	NPC473018
0.828	Intermediate Similarity	NPC325860
0.8269	Intermediate Similarity	NPC260781
0.8269	Intermediate Similarity	NPC145979
0.8269	Intermediate Similarity	NPC469707
0.8269	Intermediate Similarity	NPC469706
0.8269	Intermediate Similarity	NPC185955
0.8269	Intermediate Similarity	NPC218041
0.8269	Intermediate Similarity	NPC225815

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 NPC471403 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	894
0.2-0.3	1904
0.3-0.4	2766
0.4-0.5	1669
0.5-0.6	969
0.6-0.7	460
0.7-0.8	74
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8472	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD8455	Phase 2
0.8333	Intermediate Similarity	NPD4908	Phase 1
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD1610	Phase 2
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD8312	Approved
0.7791	Intermediate Similarity	NPD8313	Approved
0.7724	Intermediate Similarity	NPD1091	Approved
0.7718	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6674	Discontinued
0.7683	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7074	Phase 3
0.7651	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7228	Approved
0.7597	Intermediate Similarity	NPD7097	Phase 1
0.7569	Intermediate Similarity	NPD1548	Phase 1
0.755	Intermediate Similarity	NPD3027	Phase 3
0.7546	Intermediate Similarity	NPD4380	Phase 2
0.7533	Intermediate Similarity	NPD2861	Phase 2
0.753	Intermediate Similarity	NPD7768	Phase 2
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5124	Phase 1
0.7457	Intermediate Similarity	NPD7472	Approved
0.7456	Intermediate Similarity	NPD6959	Discontinued
0.7453	Intermediate Similarity	NPD7447	Phase 1
0.745	Intermediate Similarity	NPD8651	Approved
0.7438	Intermediate Similarity	NPD5058	Phase 3
0.7434	Intermediate Similarity	NPD4625	Phase 3
0.7429	Intermediate Similarity	NPD7808	Phase 3
0.7427	Intermediate Similarity	NPD6166	Phase 2
0.7427	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1653	Approved
0.7391	Intermediate Similarity	NPD7213	Phase 3
0.7391	Intermediate Similarity	NPD7212	Phase 2
0.7381	Intermediate Similarity	NPD7075	Discontinued
0.7371	Intermediate Similarity	NPD7251	Discontinued
0.7371	Intermediate Similarity	NPD6559	Discontinued
0.7358	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7199	Phase 2
0.7349	Intermediate Similarity	NPD37	Approved
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.7321	Intermediate Similarity	NPD4966	Approved
0.7314	Intermediate Similarity	NPD6797	Phase 2
0.731	Intermediate Similarity	NPD3787	Discontinued
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7273	Intermediate Similarity	NPD7240	Approved
0.7267	Intermediate Similarity	NPD4749	Approved
0.7261	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4538	Approved
0.7261	Intermediate Similarity	NPD4536	Approved
0.7233	Intermediate Similarity	NPD7266	Discontinued
0.7215	Intermediate Similarity	NPD5588	Approved
0.7215	Intermediate Similarity	NPD5960	Phase 3
0.7202	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5844	Phase 1
0.7186	Intermediate Similarity	NPD7411	Suspended
0.7186	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7843	Approved
0.7143	Intermediate Similarity	NPD1652	Phase 2
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7157	Approved
0.7104	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7819	Suspended
0.7099	Intermediate Similarity	NPD7466	Approved
0.7088	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7458	Discontinued
0.7056	Intermediate Similarity	NPD8054	Approved
0.7056	Intermediate Similarity	NPD8053	Approved
0.7051	Intermediate Similarity	NPD6798	Discontinued
0.7045	Intermediate Similarity	NPD3751	Discontinued
0.7044	Intermediate Similarity	NPD7119	Phase 2
0.7041	Intermediate Similarity	NPD6801	Discontinued
0.7041	Intermediate Similarity	NPD1934	Approved
0.7039	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7783	Phase 2
0.701	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7680	Approved
0.7	Intermediate Similarity	NPD5126	Approved
0.7	Intermediate Similarity	NPD6516	Phase 2
0.7	Intermediate Similarity	NPD5846	Approved
0.7	Intermediate Similarity	NPD5125	Phase 3
0.6995	Remote Similarity	NPD8151	Discontinued
0.6994	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1549	Phase 2
0.6964	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5403	Approved
0.6923	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5735	Approved
0.6914	Remote Similarity	NPD7229	Phase 3
0.6914	Remote Similarity	NPD5762	Approved
0.6914	Remote Similarity	NPD5763	Approved
0.6908	Remote Similarity	NPD422	Phase 1
0.6899	Remote Similarity	NPD6233	Phase 2
0.6897	Remote Similarity	NPD5494	Approved
0.6893	Remote Similarity	NPD7473	Discontinued
0.689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2684	Approved
0.6871	Remote Similarity	NPD2424	Discontinued
0.6867	Remote Similarity	NPD7041	Phase 2
0.6867	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5402	Approved
0.6852	Remote Similarity	NPD6100	Approved
0.6852	Remote Similarity	NPD6099	Approved
0.6851	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7549	Discontinued
0.6829	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5401	Approved
0.6826	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6232	Discontinued
0.6818	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8156	Discontinued
0.6807	Remote Similarity	NPD6666	Approved
0.6807	Remote Similarity	NPD6667	Approved
0.6806	Remote Similarity	NPD290	Approved
0.6802	Remote Similarity	NPD1465	Phase 2
0.6788	Remote Similarity	NPD7871	Phase 2
0.6788	Remote Similarity	NPD4628	Phase 3
0.6788	Remote Similarity	NPD4535	Phase 3
0.6788	Remote Similarity	NPD3892	Phase 2
0.6788	Remote Similarity	NPD7870	Phase 2
0.6784	Remote Similarity	NPD6072	Discontinued
0.6782	Remote Similarity	NPD3749	Approved
0.6779	Remote Similarity	NPD6671	Approved
0.6772	Remote Similarity	NPD7095	Approved
0.6761	Remote Similarity	NPD8127	Discontinued
0.676	Remote Similarity	NPD8252	Approved
0.676	Remote Similarity	NPD8251	Approved
0.676	Remote Similarity	NPD8099	Discontinued
0.6752	Remote Similarity	NPD3018	Phase 2
0.675	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD7698	Approved
0.6736	Remote Similarity	NPD7697	Approved
0.6736	Remote Similarity	NPD7696	Phase 3
0.6728	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7773	Phase 2
0.671	Remote Similarity	NPD6582	Phase 2
0.671	Remote Similarity	NPD6583	Phase 3
0.6707	Remote Similarity	NPD6002	Phase 3
0.6707	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6004	Phase 3
0.6707	Remote Similarity	NPD6005	Phase 3
0.6707	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2801	Approved
0.6688	Remote Similarity	NPD6584	Phase 3
0.6687	Remote Similarity	NPD1510	Phase 2
0.6687	Remote Similarity	NPD4108	Discontinued
0.6687	Remote Similarity	NPD7033	Discontinued
0.6687	Remote Similarity	NPD3748	Approved
0.6687	Remote Similarity	NPD7003	Approved
0.6684	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6823	Phase 2
0.6684	Remote Similarity	NPD7701	Phase 2
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD1511	Approved
0.6667	Remote Similarity	NPD3817	Phase 2
0.6667	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD6799	Approved
0.6667	Remote Similarity	NPD7037	Approved
0.6667	Remote Similarity	NPD6778	Approved
0.6667	Remote Similarity	NPD6781	Approved
0.6649	Remote Similarity	NPD7435	Discontinued
0.6646	Remote Similarity	NPD3620	Phase 2
0.6646	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2796	Approved
0.6646	Remote Similarity	NPD4140	Approved
0.6645	Remote Similarity	NPD7741	Discontinued
0.6633	Remote Similarity	NPD7584	Approved
0.6628	Remote Similarity	NPD6599	Discontinued
0.6627	Remote Similarity	NPD5061	Approved
0.6627	Remote Similarity	NPD5062	Approved
0.6624	Remote Similarity	NPD2797	Approved
0.6621	Remote Similarity	NPD968	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