NPASS Compound

Structure

NPC90472 OpenBabel07101719252D 45 50 0 0 1 0 0 0 0 0999 V2000 -1.7045 -3.0938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4513 -4.0678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3781 -1.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8898 -1.5206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5703 0.7135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5286 -2.0989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0357 0.9671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5437 0.8650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5630 -2.5809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1160 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4250 2.1843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8781 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2787 -0.3638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2302 -2.5938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4364 -3.0679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3781 -0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9954 -1.0733 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8475 1.4045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8781 1.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9818 0.4705 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2665 -1.1769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6506 0.1526 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1871 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0117 -1.5292 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8702 -1.0163 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1383 -1.0422 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2948 -2.5550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6232 -1.6743 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8552 -0.0164 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1234 -0.0424 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9356 -0.0751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0846 2.3760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1682 -3.0420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4290 2.0946 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 -6.2342 -2.5042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1609 -1.6242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8877 1.1241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2799 -1.5551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 21 2 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 41 1 0 0 0 0 13 40 1 0 0 0 0 14 22 1 0 0 0 0 15 25 1 0 0 0 0 15 26 1 0 0 0 0 16 33 1 0 0 0 0 16 42 1 0 0 0 0 17 31 1 0 0 0 0 18 22 1 0 0 0 0 18 27 2 0 0 0 0 19 36 2 0 0 0 0 19 43 1 0 0 0 0 20 37 2 0 0 0 0 20 44 1 0 0 0 0 21 32 1 0 0 0 0 22 21 1 1 0 0 0 23 14 1 1 0 0 0 23 27 1 0 0 0 0 23 40 1 0 0 0 0 24 34 1 1 0 0 0 24 35 1 0 0 0 0 25 33 1 6 0 0 0 25 43 1 0 0 0 0 26 34 1 6 0 0 0 26 44 1 0 0 0 0 27 35 1 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 28 42 1 6 0 0 0 29 33 1 1 0 0 0 29 34 1 0 0 0 0 30 35 1 6 0 0 0 30 45 1 0 0 0 0 31 38 2 0 0 0 0 31 45 1 0 0 0 0 32 39 2 0 0 0 0 32 41 1 0 0 0 0 33 6 1 1 0 0 0 34 7 1 1 0 0 0 35 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	626.31
Volume:	632.024
LogP:	3.537
LogD:	2.974
LogS:	-4.626
# Rotatable Bonds:	8
TPSA:	130.73
# H-Bond Aceptor:	10
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	5.777
Fsp3:	0.686
Lipinski Rule-of-5:	Accepted
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:	-5.175
MDCK Permeability:	5.581651930697262e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.108
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.192
Plasma Protein Binding (PPB):	91.70402526855469%
Volume Distribution (VD):	2.667
Pgp-substrate:	5.440366268157959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.356
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.78
CYP3A4-substrate:	0.592

ADMET: Excretion

Clearance (CL):	3.545
Half-life (T1/2):	0.581

ADMET: Toxicity

hERG Blockers:	0.398
Human Hepatotoxicity (H-HT):	0.94
Drug-inuced Liver Injury (DILI):	0.858
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.205
Carcinogencity:	0.005
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC90472

Natural Product ID:	NPC90472
*Common Name:**	Chisonimbolinin G
IUPAC Name:	n.a.
Synonyms:	Chisonimbolinin G
Standard InCHIKey:	RSCVHKUJNYXHPQ-BAYFQJDRSA-N
Standard InCHI:	InChI=1S/C35H46O10/c1-9-17(2)31(38)45-30-28-29-33(6,16-42-28)25(43-19(4)36)15-26(44-20(5)37)34(29,7)24-11-13-40-23-14-22(21-10-12-41-32(21)39)18(3)27(23)35(24,30)8/h9-10,22-26,28-30H,11-16H2,1-8H3/b17-9+/t22-,23+,24-,25-,26+,28-,29+,30-,33-,34+,35-/m1/s1
SMILES:	C/C=C(/C(=O)O[C@@H]1[C@@H]2OC[C@]3([C@H]2[C@]([C@@H]2[C@]1(C)C1=C(C)[C@@H](C[C@@H]1OCC2)C1=CCOC1=O)(C)[C@H](C[C@H]3OC(=O)C)OC(=O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077059
PubChem CID:	44604740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943621]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Yunnan, China	2007-May	PMID[21288727]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32208696]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[500797]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	100000.0	nM	PMID[500797]

☑ 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 NPC90472 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	275
0.1-0.2	1532
0.2-0.3	4633
0.3-0.4	7823
0.4-0.5	13822
0.5-0.6	6877
0.6-0.7	6205
0.7-0.8	1489
0.8-0.85	33
0.85-0.9	1
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9633	High Similarity	NPC469380
0.9545	High Similarity	NPC151616
0.9292	High Similarity	NPC469382
0.9211	High Similarity	NPC86346
0.9211	High Similarity	NPC469379
0.9211	High Similarity	NPC75856
0.9174	High Similarity	NPC470120
0.8696	High Similarity	NPC4548
0.8393	Intermediate Similarity	NPC253906
0.8348	Intermediate Similarity	NPC470793
0.8305	Intermediate Similarity	NPC204731
0.8288	Intermediate Similarity	NPC180744
0.8276	Intermediate Similarity	NPC284068
0.8246	Intermediate Similarity	NPC470063
0.822	Intermediate Similarity	NPC143755
0.819	Intermediate Similarity	NPC138372
0.819	Intermediate Similarity	NPC106228
0.8182	Intermediate Similarity	NPC254202
0.8174	Intermediate Similarity	NPC473535
0.8142	Intermediate Similarity	NPC469370
0.8136	Intermediate Similarity	NPC19028
0.8136	Intermediate Similarity	NPC312536
0.8136	Intermediate Similarity	NPC472667
0.8136	Intermediate Similarity	NPC9674
0.813	Intermediate Similarity	NPC470851
0.812	Intermediate Similarity	NPC473968
0.8108	Intermediate Similarity	NPC477127
0.8103	Intermediate Similarity	NPC178289
0.8091	Intermediate Similarity	NPC162973
0.8073	Intermediate Similarity	NPC471413
0.807	Intermediate Similarity	NPC475134
0.807	Intermediate Similarity	NPC475563
0.8051	Intermediate Similarity	NPC475372
0.8034	Intermediate Similarity	NPC471816
0.8017	Intermediate Similarity	NPC473979
0.8017	Intermediate Similarity	NPC469352
0.8	Intermediate Similarity	NPC471412
0.8	Intermediate Similarity	NPC475668
0.8	Intermediate Similarity	NPC473921
0.8	Intermediate Similarity	NPC472769
0.8	Intermediate Similarity	NPC474846
0.8	Intermediate Similarity	NPC469656
0.8	Intermediate Similarity	NPC475480
0.8	Intermediate Similarity	NPC469655
0.7984	Intermediate Similarity	NPC231529
0.7983	Intermediate Similarity	NPC475775
0.7983	Intermediate Similarity	NPC473636
0.7983	Intermediate Similarity	NPC475520
0.7983	Intermediate Similarity	NPC211093
0.7983	Intermediate Similarity	NPC476529
0.7983	Intermediate Similarity	NPC473839
0.7983	Intermediate Similarity	NPC77689
0.7982	Intermediate Similarity	NPC273433
0.7982	Intermediate Similarity	NPC107806
0.7982	Intermediate Similarity	NPC72647
0.7982	Intermediate Similarity	NPC471934
0.7967	Intermediate Similarity	NPC298841
0.7966	Intermediate Similarity	NPC475323
0.7966	Intermediate Similarity	NPC473656
0.7966	Intermediate Similarity	NPC10721
0.7965	Intermediate Similarity	NPC67321
0.7965	Intermediate Similarity	NPC187435
0.7949	Intermediate Similarity	NPC123117
0.7946	Intermediate Similarity	NPC189616
0.7931	Intermediate Similarity	NPC234042
0.7931	Intermediate Similarity	NPC474516
0.7931	Intermediate Similarity	NPC152117
0.7931	Intermediate Similarity	NPC269530
0.7931	Intermediate Similarity	NPC222834
0.7928	Intermediate Similarity	NPC472552
0.7928	Intermediate Similarity	NPC476081
0.792	Intermediate Similarity	NPC471170
0.7917	Intermediate Similarity	NPC107338
0.7917	Intermediate Similarity	NPC109607
0.7917	Intermediate Similarity	NPC472004
0.7909	Intermediate Similarity	NPC470761
0.7909	Intermediate Similarity	NPC473219
0.7909	Intermediate Similarity	NPC47024
0.7903	Intermediate Similarity	NPC470850
0.7899	Intermediate Similarity	NPC146280
0.7899	Intermediate Similarity	NPC124676
0.7899	Intermediate Similarity	NPC159928
0.7899	Intermediate Similarity	NPC473720
0.7895	Intermediate Similarity	NPC189075
0.7895	Intermediate Similarity	NPC275539
0.789	Intermediate Similarity	NPC475446
0.789	Intermediate Similarity	NPC311241
0.789	Intermediate Similarity	NPC100912
0.7886	Intermediate Similarity	NPC473635
0.7881	Intermediate Similarity	NPC243981
0.7881	Intermediate Similarity	NPC234858
0.7881	Intermediate Similarity	NPC154363
0.7881	Intermediate Similarity	NPC471127
0.7876	Intermediate Similarity	NPC470979
0.7876	Intermediate Similarity	NPC103088
0.7876	Intermediate Similarity	NPC470975
0.7869	Intermediate Similarity	NPC129992
0.7863	Intermediate Similarity	NPC477126
0.7851	Intermediate Similarity	NPC310511
0.7851	Intermediate Similarity	NPC52839
0.785	Intermediate Similarity	NPC475657
0.784	Intermediate Similarity	NPC472770
0.784	Intermediate Similarity	NPC175186
0.7838	Intermediate Similarity	NPC472554
0.783	Intermediate Similarity	NPC475776
0.7826	Intermediate Similarity	NPC112457
0.7826	Intermediate Similarity	NPC474243
0.7823	Intermediate Similarity	NPC42399
0.7818	Intermediate Similarity	NPC471932
0.7815	Intermediate Similarity	NPC473590
0.7815	Intermediate Similarity	NPC134430
0.7815	Intermediate Similarity	NPC475809
0.7807	Intermediate Similarity	NPC469318
0.7807	Intermediate Similarity	NPC110496
0.7807	Intermediate Similarity	NPC302788
0.7807	Intermediate Similarity	NPC473173
0.7798	Intermediate Similarity	NPC209297
0.7798	Intermediate Similarity	NPC29952
0.7798	Intermediate Similarity	NPC475380
0.7787	Intermediate Similarity	NPC257017
0.7787	Intermediate Similarity	NPC162009
0.7787	Intermediate Similarity	NPC222688
0.7778	Intermediate Similarity	NPC471446
0.7778	Intermediate Similarity	NPC473434
0.7778	Intermediate Similarity	NPC471933
0.7778	Intermediate Similarity	NPC474841
0.7778	Intermediate Similarity	NPC476716
0.7769	Intermediate Similarity	NPC329080
0.7769	Intermediate Similarity	NPC145182
0.7769	Intermediate Similarity	NPC471128
0.7769	Intermediate Similarity	NPC471126
0.7769	Intermediate Similarity	NPC470312
0.7769	Intermediate Similarity	NPC472759
0.7769	Intermediate Similarity	NPC474585
0.7769	Intermediate Similarity	NPC157252
0.7768	Intermediate Similarity	NPC295791
0.7759	Intermediate Similarity	NPC472215
0.7759	Intermediate Similarity	NPC472214
0.7759	Intermediate Similarity	NPC5284
0.7759	Intermediate Similarity	NPC179642
0.7757	Intermediate Similarity	NPC473944
0.775	Intermediate Similarity	NPC470420
0.7748	Intermediate Similarity	NPC471041
0.7742	Intermediate Similarity	NPC15095
0.7739	Intermediate Similarity	NPC306265
0.7739	Intermediate Similarity	NPC88701
0.7734	Intermediate Similarity	NPC476823
0.7731	Intermediate Similarity	NPC266728
0.7731	Intermediate Similarity	NPC72772
0.7731	Intermediate Similarity	NPC49492
0.7731	Intermediate Similarity	NPC196931
0.7731	Intermediate Similarity	NPC469794
0.7731	Intermediate Similarity	NPC477509
0.7727	Intermediate Similarity	NPC474921
0.7727	Intermediate Similarity	NPC38530
0.7727	Intermediate Similarity	NPC110937
0.7727	Intermediate Similarity	NPC84335
0.7724	Intermediate Similarity	NPC27363
0.7724	Intermediate Similarity	NPC67251
0.7724	Intermediate Similarity	NPC472399
0.7719	Intermediate Similarity	NPC173172
0.7719	Intermediate Similarity	NPC469401
0.7719	Intermediate Similarity	NPC111952
0.7719	Intermediate Similarity	NPC475414
0.7717	Intermediate Similarity	NPC34963
0.7712	Intermediate Similarity	NPC471204
0.7712	Intermediate Similarity	NPC25909
0.7712	Intermediate Similarity	NPC472757
0.7699	Intermediate Similarity	NPC61442
0.7699	Intermediate Similarity	NPC120321
0.7699	Intermediate Similarity	NPC180204
0.7698	Intermediate Similarity	NPC35109
0.7698	Intermediate Similarity	NPC104382
0.7692	Intermediate Similarity	NPC470246
0.7686	Intermediate Similarity	NPC22628
0.7686	Intermediate Similarity	NPC5989
0.7686	Intermediate Similarity	NPC475041
0.7686	Intermediate Similarity	NPC275696
0.7686	Intermediate Similarity	NPC156745
0.7686	Intermediate Similarity	NPC236918
0.7686	Intermediate Similarity	NPC5292
0.7686	Intermediate Similarity	NPC5991
0.7686	Intermediate Similarity	NPC255081
0.7686	Intermediate Similarity	NPC471108
0.768	Intermediate Similarity	NPC146456
0.768	Intermediate Similarity	NPC179412
0.768	Intermediate Similarity	NPC240070
0.768	Intermediate Similarity	NPC471356
0.768	Intermediate Similarity	NPC329784
0.768	Intermediate Similarity	NPC469757
0.768	Intermediate Similarity	NPC287423
0.768	Intermediate Similarity	NPC471357
0.768	Intermediate Similarity	NPC117702
0.7672	Intermediate Similarity	NPC284828
0.7672	Intermediate Similarity	NPC472216
0.7672	Intermediate Similarity	NPC173905
0.7672	Intermediate Similarity	NPC5475
0.7667	Intermediate Similarity	NPC53396
0.7667	Intermediate Similarity	NPC98249
0.7667	Intermediate Similarity	NPC58662

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 NPC90472 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	1773
0.2-0.3	3879
0.3-0.4	2130
0.4-0.5	706
0.5-0.6	236
0.6-0.7	173
0.7-0.8	15
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
0.7652	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7507	Approved
0.7565	Intermediate Similarity	NPD6008	Approved
0.7559	Intermediate Similarity	NPD7319	Approved
0.7458	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6686	Approved
0.7373	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7638	Approved
0.7333	Intermediate Similarity	NPD8297	Approved
0.7281	Intermediate Similarity	NPD7639	Approved
0.7281	Intermediate Similarity	NPD7640	Approved
0.7258	Intermediate Similarity	NPD7516	Approved
0.7238	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4225	Approved
0.719	Intermediate Similarity	NPD6053	Discontinued
0.7177	Intermediate Similarity	NPD7328	Approved
0.7177	Intermediate Similarity	NPD7327	Approved
0.7143	Intermediate Similarity	NPD8380	Approved
0.7143	Intermediate Similarity	NPD8335	Approved
0.7143	Intermediate Similarity	NPD8379	Approved
0.7143	Intermediate Similarity	NPD8378	Approved
0.7143	Intermediate Similarity	NPD8033	Approved
0.7143	Intermediate Similarity	NPD8296	Approved
0.7132	Intermediate Similarity	NPD7078	Approved
0.7109	Intermediate Similarity	NPD7492	Approved
0.7077	Intermediate Similarity	NPD7736	Approved
0.7063	Intermediate Similarity	NPD6054	Approved
0.7063	Intermediate Similarity	NPD8294	Approved
0.7063	Intermediate Similarity	NPD8377	Approved
0.7063	Intermediate Similarity	NPD6319	Approved
0.7054	Intermediate Similarity	NPD6616	Approved
0.7	Intermediate Similarity	NPD8293	Discontinued
0.7	Intermediate Similarity	NPD7320	Approved
0.7	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD6881	Approved
0.6992	Remote Similarity	NPD4632	Approved
0.6975	Remote Similarity	NPD6402	Approved
0.6975	Remote Similarity	NPD7128	Approved
0.6975	Remote Similarity	NPD5739	Approved
0.6975	Remote Similarity	NPD6675	Approved
0.6967	Remote Similarity	NPD6649	Approved
0.6967	Remote Similarity	NPD6650	Approved
0.6967	Remote Similarity	NPD8130	Phase 1
0.696	Remote Similarity	NPD7115	Discovery
0.6953	Remote Similarity	NPD6370	Approved
0.6942	Remote Similarity	NPD6372	Approved
0.6942	Remote Similarity	NPD6373	Approved
0.6929	Remote Similarity	NPD6059	Approved
0.6917	Remote Similarity	NPD5697	Approved
0.6911	Remote Similarity	NPD6882	Approved
0.6885	Remote Similarity	NPD7102	Approved
0.6885	Remote Similarity	NPD6883	Approved
0.6885	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD1694	Approved
0.6875	Remote Similarity	NPD6015	Approved
0.6875	Remote Similarity	NPD6016	Approved
0.686	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6903	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7900	Approved
0.6838	Remote Similarity	NPD6648	Approved
0.6829	Remote Similarity	NPD6869	Approved
0.6829	Remote Similarity	NPD6617	Approved
0.6829	Remote Similarity	NPD6847	Approved
0.6825	Remote Similarity	NPD6009	Approved
0.6822	Remote Similarity	NPD5988	Approved
0.6818	Remote Similarity	NPD7146	Approved
0.6818	Remote Similarity	NPD7521	Approved
0.6818	Remote Similarity	NPD6409	Approved
0.6818	Remote Similarity	NPD7334	Approved
0.6818	Remote Similarity	NPD5330	Approved
0.6818	Remote Similarity	NPD6684	Approved
0.6803	Remote Similarity	NPD6013	Approved
0.6803	Remote Similarity	NPD6012	Approved
0.6803	Remote Similarity	NPD6014	Approved
0.6786	Remote Similarity	NPD1695	Approved
0.6783	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5344	Discontinued
0.6777	Remote Similarity	NPD5701	Approved
0.6769	Remote Similarity	NPD7604	Phase 2
0.6748	Remote Similarity	NPD6371	Approved
0.6744	Remote Similarity	NPD5983	Phase 2
0.6726	Remote Similarity	NPD46	Approved
0.6726	Remote Similarity	NPD6698	Approved
0.6723	Remote Similarity	NPD7632	Discontinued
0.6721	Remote Similarity	NPD6011	Approved
0.6696	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6641	Remote Similarity	NPD8328	Phase 3
0.6639	Remote Similarity	NPD6412	Phase 2
0.6615	Remote Similarity	NPD7503	Approved
0.6609	Remote Similarity	NPD6399	Phase 3
0.6607	Remote Similarity	NPD3573	Approved
0.6583	Remote Similarity	NPD5211	Phase 2
0.6577	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD4696	Approved
0.6555	Remote Similarity	NPD5285	Approved
0.6555	Remote Similarity	NPD5286	Approved
0.6549	Remote Similarity	NPD5737	Approved
0.6549	Remote Similarity	NPD6672	Approved
0.6544	Remote Similarity	NPD7260	Phase 2
0.6532	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4755	Approved
0.6522	Remote Similarity	NPD6079	Approved
0.6522	Remote Similarity	NPD5693	Phase 1
0.6496	Remote Similarity	NPD6845	Suspended
0.6491	Remote Similarity	NPD5328	Approved
0.6489	Remote Similarity	NPD8513	Phase 3
0.6489	Remote Similarity	NPD8515	Approved
0.6489	Remote Similarity	NPD8517	Approved
0.6489	Remote Similarity	NPD8516	Approved
0.6484	Remote Similarity	NPD6274	Approved
0.648	Remote Similarity	NPD4634	Approved
0.6475	Remote Similarity	NPD5141	Approved
0.6462	Remote Similarity	NPD7100	Approved
0.6462	Remote Similarity	NPD7101	Approved
0.6457	Remote Similarity	NPD8133	Approved
0.6446	Remote Similarity	NPD5224	Approved
0.6446	Remote Similarity	NPD5225	Approved
0.6446	Remote Similarity	NPD5226	Approved
0.6446	Remote Similarity	NPD4633	Approved
0.6444	Remote Similarity	NPD6033	Approved
0.6435	Remote Similarity	NPD7838	Discovery
0.6434	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4700	Approved
0.641	Remote Similarity	NPD6001	Approved
0.6393	Remote Similarity	NPD5175	Approved
0.6393	Remote Similarity	NPD5174	Approved
0.6391	Remote Similarity	NPD6067	Discontinued
0.6387	Remote Similarity	NPD6083	Phase 2
0.6387	Remote Similarity	NPD6084	Phase 2
0.6385	Remote Similarity	NPD6335	Approved
0.6379	Remote Similarity	NPD8034	Phase 2
0.6379	Remote Similarity	NPD7983	Approved
0.6379	Remote Similarity	NPD7515	Phase 2
0.6379	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD6921	Approved
0.6364	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5223	Approved
0.6348	Remote Similarity	NPD6904	Approved
0.6348	Remote Similarity	NPD6051	Approved
0.6348	Remote Similarity	NPD6080	Approved
0.6348	Remote Similarity	NPD6673	Approved
0.6325	Remote Similarity	NPD5778	Approved
0.6325	Remote Similarity	NPD5779	Approved
0.632	Remote Similarity	NPD4730	Approved
0.632	Remote Similarity	NPD4729	Approved
0.6308	Remote Similarity	NPD6317	Approved
0.6303	Remote Similarity	NPD5222	Approved
0.6303	Remote Similarity	NPD5221	Approved
0.6303	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.629	Remote Similarity	NPD4767	Approved
0.629	Remote Similarity	NPD4768	Approved
0.626	Remote Similarity	NPD6313	Approved
0.626	Remote Similarity	NPD6314	Approved
0.6259	Remote Similarity	NPD8338	Approved
0.625	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD5173	Approved
0.6241	Remote Similarity	NPD6908	Approved
0.6241	Remote Similarity	NPD6909	Approved
0.6239	Remote Similarity	NPD7637	Suspended
0.6231	Remote Similarity	NPD6868	Approved
0.6228	Remote Similarity	NPD3618	Phase 1
0.622	Remote Similarity	NPD5250	Approved
0.622	Remote Similarity	NPD5247	Approved
0.622	Remote Similarity	NPD5248	Approved
0.622	Remote Similarity	NPD5249	Phase 3
0.622	Remote Similarity	NPD5251	Approved
0.6218	Remote Similarity	NPD5695	Phase 3
0.6198	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD5696	Approved
0.619	Remote Similarity	NPD5128	Approved
0.6186	Remote Similarity	NPD4202	Approved
0.6172	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4697	Phase 3
0.6154	Remote Similarity	NPD5207	Approved
0.6154	Remote Similarity	NPD5785	Approved
0.6134	Remote Similarity	NPD5282	Discontinued
0.6129	Remote Similarity	NPD4754	Approved
0.6121	Remote Similarity	NPD5208	Approved
0.6102	Remote Similarity	NPD6050	Approved
0.6102	Remote Similarity	NPD6411	Approved
0.6098	Remote Similarity	NPD1700	Approved
0.6087	Remote Similarity	NPD8337	Approved
0.6087	Remote Similarity	NPD8336	Approved
0.6087	Remote Similarity	NPD6098	Approved
0.6053	Remote Similarity	NPD3666	Approved
0.6053	Remote Similarity	NPD3665	Phase 1
0.6053	Remote Similarity	NPD3668	Phase 3
0.6053	Remote Similarity	NPD3133	Approved
0.6053	Remote Similarity	NPD4786	Approved
0.6047	Remote Similarity	NPD5215	Approved
0.6047	Remote Similarity	NPD5216	Approved
0.6047	Remote Similarity	NPD5217	Approved
0.6042	Remote Similarity	NPD6334	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