NPASS Compound

Structure

NPC105073 OpenBabel07101718272D 68 79 0 0 1 0 0 0 0 0999 V2000 0.7740 -5.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2941 -4.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1674 -4.8319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4689 -5.0039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7187 -1.2343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2218 -1.9036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4869 1.0256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2837 -0.4140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1375 -6.2517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6576 -5.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2667 -5.7766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3696 -5.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1051 -0.3665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6082 -1.0357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3180 1.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1149 0.0461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4530 -1.5034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3521 -2.7261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8436 -1.1613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7562 -1.2784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1930 -5.5161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3788 -2.3568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8293 -5.3441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5969 -0.4603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3523 -4.6204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7004 -4.4455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2771 -2.0029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4698 0.0758 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2555 -2.4326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0793 -6.3757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5018 -6.3350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0498 -0.2672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1320 0.9959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7471 -0.8677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6461 -2.0905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3788 -1.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0608 -5.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1335 -1.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0937 -4.5713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7562 -2.7162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9832 -1.3281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7300 -4.3993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6521 -0.3610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6252 -2.8651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7997 -3.5008 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9615 -3.0682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1335 -2.3568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8622 -4.0129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6224 -3.0258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6252 -1.1295 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4249 -2.0966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0937 -1.1295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0937 -2.8651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4801 -1.9973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8907 -2.8707 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6386 -0.3843 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4428 -7.2533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4025 -7.2798 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4362 0.6006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9631 1.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9446 0.0615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7427 -2.3840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2015 -1.1629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1601 -6.8472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7562 -3.6662 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9280 -1.4274 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3657 -3.6934 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 9 1 0 0 0 0 1 25 2 0 0 0 0 2 10 2 0 0 0 0 2 25 1 0 0 0 0 3 11 1 0 0 0 0 3 26 2 0 0 0 0 4 12 2 0 0 0 0 4 26 1 0 0 0 0 5 13 1 0 0 0 0 5 27 2 0 0 0 0 6 14 2 0 0 0 0 6 27 1 0 0 0 0 7 15 1 0 0 0 0 7 28 2 0 0 0 0 8 16 2 0 0 0 0 8 28 1 0 0 0 0 9 30 2 0 0 0 0 10 30 1 0 0 0 0 11 31 2 0 0 0 0 12 31 1 0 0 0 0 13 32 2 0 0 0 0 14 32 1 0 0 0 0 15 33 2 0 0 0 0 16 33 1 0 0 0 0 17 29 2 0 0 0 0 17 34 1 0 0 0 0 18 29 1 0 0 0 0 18 35 2 0 0 0 0 19 34 2 0 0 0 0 19 35 1 0 0 0 0 20 36 2 0 0 0 0 20 38 1 0 0 0 0 21 37 2 0 0 0 0 21 39 1 0 0 0 0 22 36 1 0 0 0 0 22 40 2 0 0 0 0 23 37 1 0 0 0 0 23 42 2 0 0 0 0 24 41 2 0 0 0 0 24 43 1 0 0 0 0 30 57 1 0 0 0 0 31 58 1 0 0 0 0 32 59 1 0 0 0 0 33 60 1 0 0 0 0 34 61 1 0 0 0 0 35 62 1 0 0 0 0 36 63 1 0 0 0 0 37 64 1 0 0 0 0 38 47 2 0 0 0 0 39 48 2 0 0 0 0 40 47 1 0 0 0 0 40 65 1 0 0 0 0 41 51 1 0 0 0 0 41 66 1 0 0 0 0 42 48 1 0 0 0 0 42 67 1 0 0 0 0 43 52 2 0 0 0 0 43 68 1 0 0 0 0 44 25 1 1 0 0 0 44 47 1 0 0 0 0 44 53 1 0 0 0 0 45 26 1 6 0 0 0 45 49 1 0 0 0 0 45 53 1 0 0 0 0 46 29 1 1 0 0 0 46 48 1 0 0 0 0 46 55 1 0 0 0 0 49 39 1 1 0 0 0 49 51 1 0 0 0 0 50 38 1 6 0 0 0 50 52 1 0 0 0 0 50 56 1 0 0 0 0 51 54 2 0 0 0 0 52 54 1 0 0 0 0 53 54 1 1 0 0 0 55 27 1 6 0 0 0 55 67 1 0 0 0 0 56 28 1 1 0 0 0 56 68 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	906.27
Volume:	916.662
LogP:	8.429
LogD:	4.188
LogS:	-3.981
# Rotatable Bonds:	6
TPSA:	220.76
# H-Bond Aceptor:	12
# H-Bond Donor:	10
# Rings:	12
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.075
Synthetic Accessibility Score:	5.285
Fsp3:	0.143
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:	-6.418
MDCK Permeability:	4.719721346191363e-06
Pgp-inhibitor:	0.377
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.997
20% Bioavailability (F20%):	0.578
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	94.66246795654297%
Volume Distribution (VD):	0.552
Pgp-substrate:	7.327295780181885%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.704
CYP2C19-inhibitor:	0.965
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.752
CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.832
CYP3A4-inhibitor:	0.212
CYP3A4-substrate:	0.653

ADMET: Excretion

Clearance (CL):	9.203
Half-life (T1/2):	0.222

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.184
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.955
Carcinogencity:	0.023
Eye Corrosion:	0.003
Eye Irritation:	0.912
Respiratory Toxicity:	0.012

Download Data

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

Natural Product: NPC105073

Natural Product ID:	NPC105073
*Common Name:**	Vaticaphenol A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VOANMQWFRWOKSM-IUAFFJJUSA-N
Standard InCHI:	InChI=1S/C56H42O12/c57-30-9-1-25(2-10-30)44-47-38(20-36(63)22-40(47)65)50-52-43(68-56(50)28-7-15-33(60)16-8-28)24-41(66)51-49(45(53(44)54(51)52)26-3-11-31(58)12-4-26)39-21-37(64)23-42-48(39)46(29-17-34(61)19-35(62)18-29)55(67-42)27-5-13-32(59)14-6-27/h1-24,44-46,49-50,53,55-66H/t44-,45-,46+,49-,50-,53+,55-,56+/m1/s1
SMILES:	c1cc(ccc1[C@@H]1c2c(cc(cc2O)O)[C@@H]2c3c(cc(c4[C@H](c5cc(cc6c5[C@H](c5cc(cc(c5)O)O)[C@@H](c5ccc(cc5)O)O6)O)[C@@H](c5ccc(cc5)O)[C@H]1c34)O)O[C@H]2c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524906
PubChem CID:	44575972
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO32506	Vatica oblongifolia	Species	Dipterocarpaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[12444676]

☑ 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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[531688]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	25.0	ug.mL-1	PMID[531688]

☑ 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 NPC105073 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	524
0.1-0.2	1724
0.2-0.3	4248
0.3-0.4	12004
0.4-0.5	6698
0.5-0.6	4937
0.6-0.7	8764
0.7-0.8	3287
0.8-0.85	347
0.85-0.9	115
0.9-0.95	28
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233886
1.0	High Similarity	NPC224528
0.986	High Similarity	NPC122980
0.986	High Similarity	NPC180605
0.986	High Similarity	NPC107862
0.986	High Similarity	NPC148516
0.986	High Similarity	NPC177172
0.9792	High Similarity	NPC218801
0.9724	High Similarity	NPC157081
0.972	High Similarity	NPC111134
0.9583	High Similarity	NPC112819
0.9583	High Similarity	NPC6702
0.9583	High Similarity	NPC133209
0.9524	High Similarity	NPC120633
0.9524	High Similarity	NPC473018
0.9448	High Similarity	NPC242774
0.9448	High Similarity	NPC237546
0.9448	High Similarity	NPC231712
0.9448	High Similarity	NPC224921
0.9444	High Similarity	NPC149633
0.9247	High Similarity	NPC176804
0.9247	High Similarity	NPC14468
0.9247	High Similarity	NPC71686
0.9079	High Similarity	NPC202104
0.9013	High Similarity	NPC157333
0.8966	High Similarity	NPC174787
0.8966	High Similarity	NPC213607
0.8966	High Similarity	NPC182509
0.8951	High Similarity	NPC15109
0.8951	High Similarity	NPC11727
0.8951	High Similarity	NPC125579
0.8828	High Similarity	NPC470308
0.8828	High Similarity	NPC470307
0.8759	High Similarity	NPC471522
0.8758	High Similarity	NPC476391
0.8671	High Similarity	NPC48880
0.863	High Similarity	NPC141717
0.86	High Similarity	NPC304894
0.86	High Similarity	NPC15659
0.8581	High Similarity	NPC273623
0.8552	High Similarity	NPC473665
0.8542	High Similarity	NPC238168
0.8542	High Similarity	NPC237424
0.8542	High Similarity	NPC473309
0.8533	High Similarity	NPC173203
0.8533	High Similarity	NPC163508
0.8516	High Similarity	NPC59692
0.8516	High Similarity	NPC233467
0.85	High Similarity	NPC261896
0.8497	Intermediate Similarity	NPC20757
0.8497	Intermediate Similarity	NPC227516
0.8497	Intermediate Similarity	NPC329836
0.8493	Intermediate Similarity	NPC476615
0.8493	Intermediate Similarity	NPC473107
0.8493	Intermediate Similarity	NPC476616
0.8493	Intermediate Similarity	NPC476617
0.8472	Intermediate Similarity	NPC254000
0.8452	Intermediate Similarity	NPC324517
0.8452	Intermediate Similarity	NPC329343
0.8452	Intermediate Similarity	NPC321972
0.8446	Intermediate Similarity	NPC472646
0.8446	Intermediate Similarity	NPC71465
0.8438	Intermediate Similarity	NPC90822
0.8435	Intermediate Similarity	NPC258780
0.8435	Intermediate Similarity	NPC37410
0.8403	Intermediate Similarity	NPC471519
0.8403	Intermediate Similarity	NPC471518
0.84	Intermediate Similarity	NPC277331
0.84	Intermediate Similarity	NPC100482
0.8397	Intermediate Similarity	NPC279406
0.8397	Intermediate Similarity	NPC226809
0.8387	Intermediate Similarity	NPC477612
0.8378	Intermediate Similarity	NPC133463
0.8378	Intermediate Similarity	NPC206525
0.8378	Intermediate Similarity	NPC191462
0.8378	Intermediate Similarity	NPC472648
0.8378	Intermediate Similarity	NPC472649
0.8378	Intermediate Similarity	NPC170328
0.8378	Intermediate Similarity	NPC472647
0.8355	Intermediate Similarity	NPC475492
0.8344	Intermediate Similarity	NPC224161
0.8323	Intermediate Similarity	NPC473266
0.8323	Intermediate Similarity	NPC470826
0.8323	Intermediate Similarity	NPC470098
0.8312	Intermediate Similarity	NPC204770
0.8312	Intermediate Similarity	NPC328567
0.8312	Intermediate Similarity	NPC108811
0.8312	Intermediate Similarity	NPC202742
0.8312	Intermediate Similarity	NPC327412
0.8312	Intermediate Similarity	NPC170103
0.8312	Intermediate Similarity	NPC236202
0.8312	Intermediate Similarity	NPC82917
0.8312	Intermediate Similarity	NPC320970
0.8312	Intermediate Similarity	NPC153182
0.8312	Intermediate Similarity	NPC58190
0.8312	Intermediate Similarity	NPC262911
0.8312	Intermediate Similarity	NPC294558
0.8312	Intermediate Similarity	NPC263940
0.8312	Intermediate Similarity	NPC18185
0.8312	Intermediate Similarity	NPC320671
0.8312	Intermediate Similarity	NPC70409
0.8312	Intermediate Similarity	NPC174251
0.8301	Intermediate Similarity	NPC181615
0.8299	Intermediate Similarity	NPC469610
0.8291	Intermediate Similarity	NPC46335
0.8288	Intermediate Similarity	NPC300875
0.8288	Intermediate Similarity	NPC129784
0.8288	Intermediate Similarity	NPC236014
0.8288	Intermediate Similarity	NPC207892
0.8288	Intermediate Similarity	NPC471517
0.8288	Intermediate Similarity	NPC282508
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	NPC280653
0.8288	Intermediate Similarity	NPC17343
0.8288	Intermediate Similarity	NPC271945
0.8288	Intermediate Similarity	NPC118114
0.8288	Intermediate Similarity	NPC150011
0.8288	Intermediate Similarity	NPC181497
0.8288	Intermediate Similarity	NPC196765
0.8288	Intermediate Similarity	NPC206224
0.8288	Intermediate Similarity	NPC164574
0.8288	Intermediate Similarity	NPC8899
0.8247	Intermediate Similarity	NPC96576
0.8247	Intermediate Similarity	NPC260397
0.8247	Intermediate Similarity	NPC274454
0.8247	Intermediate Similarity	NPC317053
0.8247	Intermediate Similarity	NPC215678
0.8247	Intermediate Similarity	NPC324492
0.8243	Intermediate Similarity	NPC97834
0.8243	Intermediate Similarity	NPC115335
0.8243	Intermediate Similarity	NPC225696
0.8243	Intermediate Similarity	NPC198154
0.8243	Intermediate Similarity	NPC296915
0.8243	Intermediate Similarity	NPC223008
0.8231	Intermediate Similarity	NPC469611
0.8231	Intermediate Similarity	NPC13005
0.8224	Intermediate Similarity	NPC277784
0.8219	Intermediate Similarity	NPC27187
0.8219	Intermediate Similarity	NPC470225
0.8217	Intermediate Similarity	NPC471403
0.8205	Intermediate Similarity	NPC318373
0.8205	Intermediate Similarity	NPC470208
0.8205	Intermediate Similarity	NPC321657
0.8205	Intermediate Similarity	NPC295573
0.8205	Intermediate Similarity	NPC211561
0.8205	Intermediate Similarity	NPC476969
0.82	Intermediate Similarity	NPC94994
0.82	Intermediate Similarity	NPC474687
0.8194	Intermediate Similarity	NPC9292
0.8194	Intermediate Similarity	NPC145659
0.8194	Intermediate Similarity	NPC262297
0.8153	Intermediate Similarity	NPC118000
0.8153	Intermediate Similarity	NPC205501
0.8153	Intermediate Similarity	NPC162976
0.8151	Intermediate Similarity	NPC93962
0.8137	Intermediate Similarity	NPC470827
0.8137	Intermediate Similarity	NPC147743
0.8137	Intermediate Similarity	NPC73517
0.8137	Intermediate Similarity	NPC4809
0.8137	Intermediate Similarity	NPC125495
0.8133	Intermediate Similarity	NPC3049
0.8129	Intermediate Similarity	NPC102280
0.8129	Intermediate Similarity	NPC248053
0.8129	Intermediate Similarity	NPC155564
0.8125	Intermediate Similarity	NPC113495
0.8117	Intermediate Similarity	NPC471415
0.8117	Intermediate Similarity	NPC470097
0.8117	Intermediate Similarity	NPC114119
0.8101	Intermediate Similarity	NPC259707
0.8092	Intermediate Similarity	NPC472092
0.8092	Intermediate Similarity	NPC472091
0.8092	Intermediate Similarity	NPC472090
0.8092	Intermediate Similarity	NPC221134
0.8086	Intermediate Similarity	NPC106601
0.8086	Intermediate Similarity	NPC212614
0.8086	Intermediate Similarity	NPC86630
0.8086	Intermediate Similarity	NPC151474
0.8086	Intermediate Similarity	NPC471404
0.8086	Intermediate Similarity	NPC470828
0.8086	Intermediate Similarity	NPC205613
0.8086	Intermediate Similarity	NPC159526
0.8082	Intermediate Similarity	NPC53986
0.8082	Intermediate Similarity	NPC38664
0.8082	Intermediate Similarity	NPC39064
0.8082	Intermediate Similarity	NPC47283
0.8075	Intermediate Similarity	NPC166116
0.8075	Intermediate Similarity	NPC55463
0.8069	Intermediate Similarity	NPC262573
0.8069	Intermediate Similarity	NPC471215
0.8056	Intermediate Similarity	NPC97578
0.8054	Intermediate Similarity	NPC77196
0.8054	Intermediate Similarity	NPC85435
0.8052	Intermediate Similarity	NPC184607
0.805	Intermediate Similarity	NPC46283
0.805	Intermediate Similarity	NPC272552
0.805	Intermediate Similarity	NPC322899

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 NPC105073 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	422
0.1-0.2	970
0.2-0.3	1728
0.3-0.4	2802
0.4-0.5	1678
0.5-0.6	978
0.6-0.7	499
0.7-0.8	69
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8345	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD4908	Phase 1
0.7891	Intermediate Similarity	NPD2861	Phase 2
0.7847	Intermediate Similarity	NPD1610	Phase 2
0.7785	Intermediate Similarity	NPD4625	Phase 3
0.7576	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1548	Phase 1
0.756	Intermediate Similarity	NPD7199	Phase 2
0.756	Intermediate Similarity	NPD6959	Discontinued
0.7532	Intermediate Similarity	NPD3892	Phase 2
0.7516	Intermediate Similarity	NPD1613	Approved
0.7516	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5735	Approved
0.7425	Intermediate Similarity	NPD7768	Phase 2
0.7419	Intermediate Similarity	NPD6353	Approved
0.7383	Intermediate Similarity	NPD5327	Phase 3
0.7383	Intermediate Similarity	NPD4749	Approved
0.7368	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7447	Phase 1
0.7341	Intermediate Similarity	NPD7228	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
0.731	Intermediate Similarity	NPD7229	Phase 3
0.7305	Intermediate Similarity	NPD7819	Suspended
0.7303	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7037	Approved
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7284	Intermediate Similarity	NPD7212	Phase 2
0.7284	Intermediate Similarity	NPD7213	Phase 3
0.7267	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5763	Approved
0.7233	Intermediate Similarity	NPD5762	Approved
0.7225	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3027	Phase 3
0.7205	Intermediate Similarity	NPD7466	Approved
0.7202	Intermediate Similarity	NPD8455	Phase 2
0.7197	Intermediate Similarity	NPD2157	Approved
0.7179	Intermediate Similarity	NPD4140	Approved
0.7178	Intermediate Similarity	NPD7041	Phase 2
0.7178	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD37	Approved
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.7105	Intermediate Similarity	NPD6696	Suspended
0.7099	Intermediate Similarity	NPD3750	Approved
0.7095	Intermediate Similarity	NPD7741	Discontinued
0.7095	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD8313	Approved
0.7063	Intermediate Similarity	NPD6100	Approved
0.7063	Intermediate Similarity	NPD6099	Approved
0.7051	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6674	Discontinued
0.703	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4624	Approved
0.7006	Intermediate Similarity	NPD5844	Phase 1
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD8651	Approved
0.6983	Remote Similarity	NPD7240	Approved
0.6982	Remote Similarity	NPD7411	Suspended
0.6981	Remote Similarity	NPD4097	Suspended
0.6977	Remote Similarity	NPD3749	Approved
0.6964	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3620	Phase 2
0.6962	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8054	Approved
0.6961	Remote Similarity	NPD8053	Approved
0.6954	Remote Similarity	NPD8127	Discontinued
0.6944	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6166	Phase 2
0.6932	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4380	Phase 2
0.6914	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6005	Phase 3
0.6914	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6004	Phase 3
0.6914	Remote Similarity	NPD6002	Phase 3
0.6903	Remote Similarity	NPD6584	Phase 3
0.6893	Remote Similarity	NPD7473	Discontinued
0.689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6273	Approved
0.6882	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7831	Phase 2
0.6879	Remote Similarity	NPD7833	Phase 2
0.6879	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7075	Discontinued
0.6871	Remote Similarity	NPD1549	Phase 2
0.6867	Remote Similarity	NPD3091	Approved
0.6867	Remote Similarity	NPD7390	Discontinued
0.6839	Remote Similarity	NPD3094	Phase 2
0.6835	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7119	Phase 2
0.6832	Remote Similarity	NPD7097	Phase 1
0.6831	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7680	Approved
0.6818	Remote Similarity	NPD6232	Discontinued
0.6816	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8156	Discontinued
0.6813	Remote Similarity	NPD6355	Discontinued
0.68	Remote Similarity	NPD5494	Approved
0.6797	Remote Similarity	NPD422	Phase 1
0.6797	Remote Similarity	NPD3092	Approved
0.6796	Remote Similarity	NPD6559	Discontinued
0.6792	Remote Similarity	NPD8032	Phase 2
0.679	Remote Similarity	NPD5588	Approved
0.679	Remote Similarity	NPD3748	Approved
0.6788	Remote Similarity	NPD7003	Approved
0.6779	Remote Similarity	NPD6671	Approved
0.6765	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.676	Remote Similarity	NPD8252	Approved
0.676	Remote Similarity	NPD8251	Approved
0.676	Remote Similarity	NPD8099	Discontinued
0.6752	Remote Similarity	NPD5736	Approved
0.6752	Remote Similarity	NPD3018	Phase 2
0.6744	Remote Similarity	NPD1934	Approved
0.6727	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2533	Approved
0.6726	Remote Similarity	NPD2534	Approved
0.6726	Remote Similarity	NPD7019	Approved
0.6726	Remote Similarity	NPD7020	Approved
0.6726	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2532	Approved
0.6723	Remote Similarity	NPD3787	Discontinued
0.672	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6582	Phase 2
0.671	Remote Similarity	NPD6583	Phase 3
0.6705	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD7843	Approved
0.6687	Remote Similarity	NPD1510	Phase 2
0.6687	Remote Similarity	NPD6663	Approved
0.6687	Remote Similarity	NPD7033	Discontinued
0.6686	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD3095	Discontinued
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD3818	Discontinued
0.6667	Remote Similarity	NPD7906	Approved
0.6667	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7157	Approved
0.6647	Remote Similarity	NPD7427	Discontinued
0.6646	Remote Similarity	NPD2796	Approved
0.6646	Remote Similarity	NPD2238	Phase 2
0.663	Remote Similarity	NPD7054	Approved
0.6629	Remote Similarity	NPD3882	Suspended
0.6629	Remote Similarity	NPD7773	Phase 2
0.6626	Remote Similarity	NPD4536	Approved
0.6626	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4538	Approved
0.6625	Remote Similarity	NPD6798	Discontinued
0.6623	Remote Similarity	NPD7340	Approved
0.6615	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD1653	Approved
0.6607	Remote Similarity	NPD6667	Approved
0.6607	Remote Similarity	NPD5058	Phase 3
0.6607	Remote Similarity	NPD6666	Approved
0.6603	Remote Similarity	NPD2982	Phase 2
0.6603	Remote Similarity	NPD2983	Phase 2
0.6601	Remote Similarity	NPD5691	Approved
0.6599	Remote Similarity	NPD4750	Phase 3
0.6595	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7472	Approved
0.6592	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6331	Phase 2
0.6585	Remote Similarity	NPD4108	Discontinued
0.6585	Remote Similarity	NPD5960	Phase 3
0.6581	Remote Similarity	NPD1091	Approved
0.6576	Remote Similarity	NPD7549	Discontinued
0.6576	Remote Similarity	NPD7808	Phase 3
0.6575	Remote Similarity	NPD2342	Discontinued
0.6568	Remote Similarity	NPD1511	Approved
0.6562	Remote Similarity	NPD7095	Approved
0.6561	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD6516	Phase 2
0.6558	Remote Similarity	NPD5846	Approved
0.6558	Remote Similarity	NPD4059	Approved
0.6552	Remote Similarity	NPD6801	Discontinued
0.6545	Remote Similarity	NPD5404	Approved
0.6545	Remote Similarity	NPD5406	Approved
0.6545	Remote Similarity	NPD5405	Approved
0.6545	Remote Similarity	NPD4477	Approved
0.6545	Remote Similarity	NPD5408	Approved
0.6545	Remote Similarity	NPD4476	Approved
0.6541	Remote Similarity	NPD7310	Approved
0.6541	Remote Similarity	NPD7312	Approved
0.6541	Remote Similarity	NPD4578	Approved
0.6541	Remote Similarity	NPD1712	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