NPASS Compound

Structure

NPC472680 OpenBabel07101719132D 43 47 0 0 1 0 0 0 0 0999 V2000 3.8461 5.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9095 6.9903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8943 1.5150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3939 -0.1048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5866 4.6141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8619 -1.3983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5276 -0.6809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0518 -1.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8835 -1.6716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4051 0.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5652 1.4283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3899 -0.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8901 5.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4108 6.1983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9121 5.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7101 0.9522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5348 -0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 3.7122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3280 2.8835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9083 0.4356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1883 0.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3888 6.1617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6765 0.5609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3914 4.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6949 -0.0263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7413 0.2724 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6198 -0.4997 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2995 -0.1723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8399 -0.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8525 -0.6855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9970 1.1530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2885 0.9352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0711 0.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5734 -0.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6657 -0.7174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2426 1.1530 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4674 0.5632 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8247 -1.4810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6348 -1.6396 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4217 2.0348 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3772 1.6526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8533 1.9480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 34 1 0 0 0 0 7 34 1 0 0 0 0 8 35 1 0 0 0 0 9 35 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 22 2 0 0 0 0 15 24 1 0 0 0 0 16 25 2 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 20 36 1 0 0 0 0 21 26 1 0 0 0 0 21 37 1 0 0 0 0 25 29 1 0 0 0 0 26 23 1 6 0 0 0 26 34 1 0 0 0 0 27 20 1 1 0 0 0 27 28 1 0 0 0 0 27 35 1 0 0 0 0 28 30 1 0 0 0 0 28 37 1 1 0 0 0 29 39 2 0 0 0 0 30 34 1 0 0 0 0 30 40 1 6 0 0 0 31 36 1 0 0 0 0 31 37 1 0 0 0 0 31 41 2 0 0 0 0 32 36 1 0 0 0 0 32 38 1 0 0 0 0 32 42 2 0 0 0 0 33 37 1 0 0 0 0 33 38 1 0 0 0 0 33 43 2 0 0 0 0 35 38 1 0 0 0 0 36 19 1 1 0 0 0 38 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.37
Volume:	643.245
LogP:	7.449
LogD:	6.015
LogS:	-5.153
# Rotatable Bonds:	8
TPSA:	88.51
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.195
Synthetic Accessibility Score:	6.615
Fsp3:	0.632
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.296
MDCK Permeability:	1.857918869063724e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.485
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	99.8558120727539%
Volume Distribution (VD):	1.679
Pgp-substrate:	4.549653053283691%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.655
CYP2C19-inhibitor:	0.598
CYP2C19-substrate:	0.965
CYP2C9-inhibitor:	0.772
CYP2C9-substrate:	0.964
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.045
CYP3A4-inhibitor:	0.689
CYP3A4-substrate:	0.932

ADMET: Excretion

Clearance (CL):	6.145
Half-life (T1/2):	0.101

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.918
AMES Toxicity:	0.128
Rat Oral Acute Toxicity:	0.636
Maximum Recommended Daily Dose:	0.06
Skin Sensitization:	0.021
Carcinogencity:	0.046
Eye Corrosion:	0.042
Eye Irritation:	0.041
Respiratory Toxicity:	0.857

Download Data

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

Natural Product: NPC472680

Natural Product ID:	NPC472680
*Common Name:**	DEQAWTTZWHYRGD-PMTQRNBPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DEQAWTTZWHYRGD-PMTQRNBPSA-N
Standard InCHI:	InChI=1S/C38H50O5/c1-22(2)14-13-15-24(5)18-19-36-20-27-28-30(40)34(6,7)26(23(3)4)21-37(28,31(36)41)33(43)38(32(36)42,35(27,8)9)29(39)25-16-11-10-12-17-25/h10-12,14,16-18,23,26-28,30,40H,13,15,19-21H2,1-9H3/b24-18+/t26-,27-,28-,30-,36+,37?,38+/m1/s1
SMILES:	C/C(=CC[C@]12C[C@@H]3[C@H]4C(C1=O)(C[C@@H](C([C@@H]4O)(C)C)C(C)C)C(=O)[C@](C2=O)(C3(C)C)C(=O)c1ccccc1)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581577
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	13300.0	nM	PMID[506276]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	14200.0	nM	PMID[506276]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	14500.0	nM	PMID[506276]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	17600.0	nM	PMID[506276]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	19100.0	nM	PMID[506276]

☑ 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 NPC472680 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	272
0.1-0.2	1177
0.2-0.3	2501
0.3-0.4	7511
0.4-0.5	13810
0.5-0.6	14444
0.6-0.7	2705
0.7-0.8	261
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472679
0.9655	High Similarity	NPC472681
0.8908	High Similarity	NPC476234
0.8547	High Similarity	NPC130591
0.8547	High Similarity	NPC234637
0.8482	Intermediate Similarity	NPC475939
0.8482	Intermediate Similarity	NPC471829
0.8482	Intermediate Similarity	NPC472691
0.8482	Intermediate Similarity	NPC474866
0.8475	Intermediate Similarity	NPC215419
0.8462	Intermediate Similarity	NPC471481
0.8448	Intermediate Similarity	NPC265513
0.8376	Intermediate Similarity	NPC218855
0.8359	Intermediate Similarity	NPC471334
0.8347	Intermediate Similarity	NPC472698
0.8347	Intermediate Similarity	NPC472697
0.8305	Intermediate Similarity	NPC470253
0.8268	Intermediate Similarity	NPC472678
0.8189	Intermediate Similarity	NPC171007
0.8189	Intermediate Similarity	NPC190849
0.8189	Intermediate Similarity	NPC470648
0.8151	Intermediate Similarity	NPC93287
0.813	Intermediate Similarity	NPC476645
0.813	Intermediate Similarity	NPC202015
0.8125	Intermediate Similarity	NPC316553
0.8115	Intermediate Similarity	NPC61651
0.8047	Intermediate Similarity	NPC470753
0.8047	Intermediate Similarity	NPC474106
0.8047	Intermediate Similarity	NPC473220
0.8031	Intermediate Similarity	NPC472693
0.8031	Intermediate Similarity	NPC472694
0.803	Intermediate Similarity	NPC203486
0.8	Intermediate Similarity	NPC475138
0.7969	Intermediate Similarity	NPC294050
0.7969	Intermediate Similarity	NPC470765
0.7969	Intermediate Similarity	NPC328997
0.7967	Intermediate Similarity	NPC80605
0.7967	Intermediate Similarity	NPC323440
0.7967	Intermediate Similarity	NPC268930
0.7967	Intermediate Similarity	NPC222968
0.7953	Intermediate Similarity	NPC325740
0.7934	Intermediate Similarity	NPC294458
0.7934	Intermediate Similarity	NPC471721
0.7917	Intermediate Similarity	NPC471189
0.7917	Intermediate Similarity	NPC280789
0.7907	Intermediate Similarity	NPC146239
0.7907	Intermediate Similarity	NPC169913
0.7895	Intermediate Similarity	NPC18982
0.7895	Intermediate Similarity	NPC126516
0.7895	Intermediate Similarity	NPC475346
0.7895	Intermediate Similarity	NPC475457
0.7895	Intermediate Similarity	NPC475627
0.7895	Intermediate Similarity	NPC329913
0.7891	Intermediate Similarity	NPC478108
0.7881	Intermediate Similarity	NPC472696
0.7881	Intermediate Similarity	NPC472701
0.7881	Intermediate Similarity	NPC472683
0.7881	Intermediate Similarity	NPC472695
0.7863	Intermediate Similarity	NPC471186
0.7836	Intermediate Similarity	NPC474659
0.7829	Intermediate Similarity	NPC275576
0.7826	Intermediate Similarity	NPC477468
0.7815	Intermediate Similarity	NPC470252
0.7812	Intermediate Similarity	NPC328107
0.7805	Intermediate Similarity	NPC260886
0.7803	Intermediate Similarity	NPC472692
0.7803	Intermediate Similarity	NPC472682
0.7797	Intermediate Similarity	NPC472699
0.7797	Intermediate Similarity	NPC472700
0.7761	Intermediate Similarity	NPC48929
0.776	Intermediate Similarity	NPC318173
0.7742	Intermediate Similarity	NPC469843
0.7727	Intermediate Similarity	NPC25736
0.7717	Intermediate Similarity	NPC472981
0.771	Intermediate Similarity	NPC478165
0.771	Intermediate Similarity	NPC478162
0.7692	Intermediate Similarity	NPC247976
0.7687	Intermediate Similarity	NPC144257
0.7674	Intermediate Similarity	NPC85511
0.7656	Intermediate Similarity	NPC269923
0.7656	Intermediate Similarity	NPC167323
0.7647	Intermediate Similarity	NPC100767
0.7638	Intermediate Similarity	NPC476225
0.7627	Intermediate Similarity	NPC329282
0.7623	Intermediate Similarity	NPC471188
0.7609	Intermediate Similarity	NPC469681
0.7609	Intermediate Similarity	NPC469680
0.7609	Intermediate Similarity	NPC471974
0.7591	Intermediate Similarity	NPC249817
0.7583	Intermediate Similarity	NPC211439
0.7576	Intermediate Similarity	NPC115797
0.7576	Intermediate Similarity	NPC51448
0.7574	Intermediate Similarity	NPC23894
0.7561	Intermediate Similarity	NPC143768
0.7556	Intermediate Similarity	NPC472656
0.7538	Intermediate Similarity	NPC318067
0.7538	Intermediate Similarity	NPC140118
0.7538	Intermediate Similarity	NPC12881
0.7536	Intermediate Similarity	NPC475482
0.7536	Intermediate Similarity	NPC22676
0.7536	Intermediate Similarity	NPC475957
0.7536	Intermediate Similarity	NPC216940
0.7536	Intermediate Similarity	NPC198621
0.7521	Intermediate Similarity	NPC109514
0.7521	Intermediate Similarity	NPC476993
0.752	Intermediate Similarity	NPC9274
0.7519	Intermediate Similarity	NPC225103
0.7518	Intermediate Similarity	NPC469855
0.7518	Intermediate Similarity	NPC477874
0.7518	Intermediate Similarity	NPC471972
0.7518	Intermediate Similarity	NPC471971
0.7518	Intermediate Similarity	NPC173569
0.7518	Intermediate Similarity	NPC30846
0.75	Intermediate Similarity	NPC94751
0.75	Intermediate Similarity	NPC317280
0.75	Intermediate Similarity	NPC142326
0.75	Intermediate Similarity	NPC329387
0.7478	Intermediate Similarity	NPC219573
0.7478	Intermediate Similarity	NPC185208
0.7466	Intermediate Similarity	NPC304876
0.7466	Intermediate Similarity	NPC472005
0.7466	Intermediate Similarity	NPC242262
0.7466	Intermediate Similarity	NPC265395
0.7466	Intermediate Similarity	NPC472022
0.7466	Intermediate Similarity	NPC472030
0.7466	Intermediate Similarity	NPC473414
0.7466	Intermediate Similarity	NPC1173
0.7466	Intermediate Similarity	NPC256142
0.7466	Intermediate Similarity	NPC249471
0.7466	Intermediate Similarity	NPC158333
0.7466	Intermediate Similarity	NPC237549
0.7466	Intermediate Similarity	NPC257213
0.7463	Intermediate Similarity	NPC473443
0.7463	Intermediate Similarity	NPC472388
0.7445	Intermediate Similarity	NPC477893
0.7445	Intermediate Similarity	NPC477896
0.7438	Intermediate Similarity	NPC470007
0.7438	Intermediate Similarity	NPC112903
0.7436	Intermediate Similarity	NPC54647
0.7432	Intermediate Similarity	NPC469771
0.7431	Intermediate Similarity	NPC143685
0.7431	Intermediate Similarity	NPC301556
0.7431	Intermediate Similarity	NPC266265
0.7431	Intermediate Similarity	NPC92293
0.7431	Intermediate Similarity	NPC270590
0.7431	Intermediate Similarity	NPC471101
0.7426	Intermediate Similarity	NPC472437
0.7424	Intermediate Similarity	NPC478107
0.7424	Intermediate Similarity	NPC470649
0.7415	Intermediate Similarity	NPC114410
0.7415	Intermediate Similarity	NPC26033
0.7415	Intermediate Similarity	NPC112523
0.7415	Intermediate Similarity	NPC228204
0.7414	Intermediate Similarity	NPC324602
0.7414	Intermediate Similarity	NPC239185
0.7414	Intermediate Similarity	NPC240042
0.7413	Intermediate Similarity	NPC469854
0.7413	Intermediate Similarity	NPC469856
0.741	Intermediate Similarity	NPC118366
0.741	Intermediate Similarity	NPC472395
0.741	Intermediate Similarity	NPC472371
0.7407	Intermediate Similarity	NPC470278
0.7407	Intermediate Similarity	NPC472361
0.7402	Intermediate Similarity	NPC152812
0.7395	Intermediate Similarity	NPC329556
0.7394	Intermediate Similarity	NPC475122
0.7394	Intermediate Similarity	NPC111466
0.7394	Intermediate Similarity	NPC477209
0.7391	Intermediate Similarity	NPC472374
0.7391	Intermediate Similarity	NPC472372
0.7379	Intermediate Similarity	NPC325032
0.7379	Intermediate Similarity	NPC7095
0.7379	Intermediate Similarity	NPC477483
0.7376	Intermediate Similarity	NPC27518
0.7376	Intermediate Similarity	NPC304110
0.7373	Intermediate Similarity	NPC128248
0.7373	Intermediate Similarity	NPC133809
0.7373	Intermediate Similarity	NPC136810
0.7368	Intermediate Similarity	NPC59677
0.7361	Intermediate Similarity	NPC281717
0.736	Intermediate Similarity	NPC196673
0.7357	Intermediate Similarity	NPC234548
0.7357	Intermediate Similarity	NPC248287
0.7355	Intermediate Similarity	NPC83409
0.7355	Intermediate Similarity	NPC185763
0.7355	Intermediate Similarity	NPC85560
0.7355	Intermediate Similarity	NPC244933
0.7353	Intermediate Similarity	NPC80599
0.735	Intermediate Similarity	NPC134882
0.7347	Intermediate Similarity	NPC77719
0.7343	Intermediate Similarity	NPC472556
0.7343	Intermediate Similarity	NPC472572
0.7343	Intermediate Similarity	NPC472575
0.7343	Intermediate Similarity	NPC200471
0.7343	Intermediate Similarity	NPC471104
0.7343	Intermediate Similarity	NPC70403
0.7343	Intermediate Similarity	NPC470159
0.7343	Intermediate Similarity	NPC472568
0.7343	Intermediate Similarity	NPC476973
0.7343	Intermediate Similarity	NPC158663

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 NPC472680 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	850
0.2-0.3	1591
0.3-0.4	3219
0.4-0.5	2276
0.5-0.6	881
0.6-0.7	74
0.7-0.8	6
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
0.8115	Intermediate Similarity	NPD7610	Discontinued
0.7983	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7961	Discontinued
0.7561	Intermediate Similarity	NPD7094	Approved
0.7561	Intermediate Similarity	NPD6858	Approved
0.748	Intermediate Similarity	NPD7009	Phase 2
0.7414	Intermediate Similarity	NPD3495	Discontinued
0.7395	Intermediate Similarity	NPD1929	Approved
0.7395	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD1930	Approved
0.7311	Intermediate Similarity	NPD1932	Approved
0.7308	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5951	Approved
0.7288	Intermediate Similarity	NPD2066	Phase 3
0.7236	Intermediate Similarity	NPD2329	Discontinued
0.7222	Intermediate Similarity	NPD7236	Approved
0.7217	Intermediate Similarity	NPD7631	Approved
0.7206	Intermediate Similarity	NPD7008	Discontinued
0.7155	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7609	Phase 3
0.7099	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8166	Discontinued
0.7049	Intermediate Similarity	NPD1237	Approved
0.698	Remote Similarity	NPD7239	Suspended
0.697	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6647	Phase 2
0.6957	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4879	Approved
0.6905	Remote Similarity	NPD1317	Discontinued
0.6899	Remote Similarity	NPD2629	Approved
0.6849	Remote Similarity	NPD7003	Approved
0.6846	Remote Similarity	NPD3317	Approved
0.6838	Remote Similarity	NPD7515	Phase 2
0.6821	Remote Similarity	NPD7458	Discontinued
0.6815	Remote Similarity	NPD4878	Approved
0.6788	Remote Similarity	NPD1470	Approved
0.6783	Remote Similarity	NPD650	Approved
0.678	Remote Similarity	NPD1088	Approved
0.6759	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD7715	Approved
0.6738	Remote Similarity	NPD7714	Approved
0.6733	Remote Similarity	NPD6273	Approved
0.6723	Remote Similarity	NPD7748	Approved
0.6721	Remote Similarity	NPD7798	Approved
0.6716	Remote Similarity	NPD3019	Approved
0.6694	Remote Similarity	NPD7902	Approved
0.6692	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7084	Phase 3
0.6667	Remote Similarity	NPD1693	Approved
0.6639	Remote Similarity	NPD1508	Approved
0.6621	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7713	Phase 3
0.6618	Remote Similarity	NPD1201	Approved
0.661	Remote Similarity	NPD1089	Approved
0.661	Remote Similarity	NPD1086	Approved
0.661	Remote Similarity	NPD1090	Approved
0.6593	Remote Similarity	NPD2932	Approved
0.6589	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7058	Phase 2
0.6561	Remote Similarity	NPD7057	Phase 3
0.656	Remote Similarity	NPD5765	Approved
0.6549	Remote Similarity	NPD942	Approved
0.6544	Remote Similarity	NPD3026	Approved
0.6544	Remote Similarity	NPD3023	Approved
0.6535	Remote Similarity	NPD6685	Approved
0.6529	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5347	Phase 2
0.6525	Remote Similarity	NPD5346	Phase 2
0.6525	Remote Similarity	NPD800	Approved
0.6522	Remote Similarity	NPD5157	Phase 1
0.6522	Remote Similarity	NPD5159	Phase 2
0.6522	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3025	Approved
0.6519	Remote Similarity	NPD3024	Approved
0.6508	Remote Similarity	NPD5909	Discontinued
0.6503	Remote Similarity	NPD6663	Approved
0.65	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.649	Remote Similarity	NPD8165	Discontinued
0.6475	Remote Similarity	NPD1989	Approved
0.6475	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1843	Approved
0.6471	Remote Similarity	NPD2345	Approved
0.6463	Remote Similarity	NPD5405	Approved
0.6463	Remote Similarity	NPD5404	Approved
0.6463	Remote Similarity	NPD5408	Approved
0.6463	Remote Similarity	NPD5406	Approved
0.6454	Remote Similarity	NPD5736	Approved
0.6447	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7900	Approved
0.6446	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7741	Discontinued
0.6439	Remote Similarity	NPD6010	Discontinued
0.6434	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD2182	Approved
0.6423	Remote Similarity	NPD1564	Approved
0.6423	Remote Similarity	NPD1566	Phase 3
0.6423	Remote Similarity	NPD1565	Approved
0.6417	Remote Similarity	NPD1239	Approved
0.6417	Remote Similarity	NPD6079	Approved
0.6412	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3618	Phase 1
0.6408	Remote Similarity	NPD7055	Discontinued
0.6402	Remote Similarity	NPD7799	Discontinued
0.6397	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7305	Phase 1
0.6387	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7390	Discontinued
0.6377	Remote Similarity	NPD6287	Discontinued
0.6356	Remote Similarity	NPD4793	Discontinued
0.6356	Remote Similarity	NPD1087	Approved
0.635	Remote Similarity	NPD4199	Phase 3
0.635	Remote Similarity	NPD3095	Discontinued
0.6345	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD3673	Approved
0.6333	Remote Similarity	NPD3672	Approved
0.6331	Remote Similarity	NPD3972	Approved
0.6328	Remote Similarity	NPD5048	Discontinued
0.6324	Remote Similarity	NPD3091	Approved
0.6319	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD2346	Discontinued
0.6299	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD8127	Discontinued
0.6289	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD8312	Approved
0.6272	Remote Similarity	NPD8313	Approved
0.627	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD2798	Approved
0.6261	Remote Similarity	NPD226	Approved
0.626	Remote Similarity	NPD6049	Phase 2
0.626	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.626	Remote Similarity	NPD4629	Approved
0.626	Remote Similarity	NPD5210	Approved
0.6259	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6065	Approved
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7295	Approved
0.625	Remote Similarity	NPD164	Approved
0.6232	Remote Similarity	NPD7725	Approved
0.6225	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4198	Discontinued
0.621	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.621	Remote Similarity	NPD5222	Approved
0.621	Remote Similarity	NPD5221	Approved
0.6184	Remote Similarity	NPD4628	Phase 3
0.6179	Remote Similarity	NPD1563	Approved
0.6179	Remote Similarity	NPD1202	Approved
0.6178	Remote Similarity	NPD3226	Approved
0.6174	Remote Similarity	NPD2799	Discontinued
0.6174	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD6912	Phase 3
0.6163	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.616	Remote Similarity	NPD5173	Approved
0.6154	Remote Similarity	NPD9491	Approved
0.6154	Remote Similarity	NPD6085	Phase 2
0.6154	Remote Similarity	NPD8368	Discontinued
0.6154	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD3092	Approved
0.6138	Remote Similarity	NPD6966	Discovery
0.6127	Remote Similarity	NPD1876	Approved
0.6118	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD5836	Discontinued
0.6111	Remote Similarity	NPD9495	Approved
0.6104	Remote Similarity	NPD3300	Phase 2
0.6102	Remote Similarity	NPD3665	Phase 1
0.6102	Remote Similarity	NPD3666	Approved
0.6102	Remote Similarity	NPD3133	Approved
0.6099	Remote Similarity	NPD6637	Approved
0.6096	Remote Similarity	NPD2313	Discontinued
0.6096	Remote Similarity	NPD3764	Approved
0.6094	Remote Similarity	NPD2193	Phase 2
0.6094	Remote Similarity	NPD2648	Phase 3
0.6093	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD1471	Phase 3
0.6092	Remote Similarity	NPD8360	Approved
0.6092	Remote Similarity	NPD8361	Approved
0.6092	Remote Similarity	NPD8435	Approved
0.609	Remote Similarity	NPD3643	Approved
0.609	Remote Similarity	NPD3644	Approved
0.609	Remote Similarity	NPD3642	Approved
0.6084	Remote Similarity	NPD3094	Phase 2
0.608	Remote Similarity	NPD4697	Phase 3
0.6077	Remote Similarity	NPD1018	Approved
0.6076	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD8434	Phase 2
0.6069	Remote Similarity	NPD8150	Discontinued
0.6067	Remote Similarity	NPD8485	Approved
0.6066	Remote Similarity	NPD9256	Approved
0.6066	Remote Similarity	NPD9258	Approved
0.6063	Remote Similarity	NPD5286	Approved
0.6063	Remote Similarity	NPD4696	Approved
0.6063	Remote Similarity	NPD1238	Approved
0.6063	Remote Similarity	NPD5285	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