NPASS Compound

Structure

CID150057 OpenBabel06191715522D 62 70 0 0 1 0 0 0 0 0999 V2000 1.7086 8.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5935 5.1947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3775 -2.9258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5614 1.1193 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.4411 -0.4777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1382 1.7192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7315 2.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2086 8.0482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3749 -0.7078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1547 2.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9681 0.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2521 2.9463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2914 7.1822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9572 -0.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7370 4.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7086 7.1822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7506 -6.5800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4140 -5.1710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2086 8.0482 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6153 5.4026 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7897 -2.1168 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5504 0.9102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3694 -0.8124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7370 2.7373 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1492 1.9283 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3302 3.6508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9938 5.2335 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1573 -5.6665 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.0073 -4.2575 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1278 4.7335 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1965 -1.2033 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.1518 -5.5619 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0128 -4.1530 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6087 -0.3943 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5586 -4.6484 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6142 -0.4988 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.9708 -3.8394 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6060 -3.2394 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1938 -2.4304 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.2074 -1.4123 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9763 -3.9439 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1884 -2.5349 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.5559 1.0147 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3357 3.7554 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2086 6.3162 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2086 6.3162 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3384 -7.3890 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8263 -5.9801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1910 -1.0987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7396 -6.3710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4250 -4.9620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0154 0.5193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5531 -4.5439 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0264 0.3102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3775 -2.9258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7952 -2.2213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7761 -1.7259 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5695 -4.8575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5951 -3.4485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3885 -3.1349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7871 -1.5169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7859 6.2117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 6 7 1 0 0 0 0 6 22 2 0 0 0 0 8 13 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 25 1 0 0 0 0 11 43 1 0 0 0 0 12 44 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 46 1 0 0 0 0 17 28 1 0 0 0 0 17 47 1 0 0 0 0 18 29 1 0 0 0 0 18 48 1 0 0 0 0 19 1 1 6 0 0 0 20 30 1 0 0 0 0 20 45 1 1 0 0 0 21 31 1 0 0 0 0 21 56 1 0 0 0 0 22 43 1 0 0 0 0 23 57 1 6 0 0 0 24 7 1 1 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 25 43 1 6 0 0 0 26 44 1 6 0 0 0 27 15 1 6 0 0 0 27 30 1 0 0 0 0 27 62 1 0 0 0 0 28 32 1 0 0 0 0 28 58 1 0 0 0 0 29 33 1 0 0 0 0 29 59 1 0 0 0 0 30 44 1 6 0 0 0 31 34 1 0 0 0 0 31 49 1 0 0 0 0 32 35 1 0 0 0 0 32 50 1 0 0 0 0 33 38 1 0 0 0 0 33 51 1 0 0 0 0 34 36 1 0 0 0 0 34 52 1 0 0 0 0 35 37 1 0 0 0 0 35 53 1 0 0 0 0 36 40 1 0 0 0 0 36 54 1 0 0 0 0 37 41 1 0 0 0 0 37 55 1 0 0 0 0 38 39 1 0 0 0 0 38 60 1 0 0 0 0 39 42 1 0 0 0 0 39 61 1 0 0 0 0 40 56 1 0 0 0 0 40 61 1 0 0 0 0 41 58 1 0 0 0 0 41 60 1 0 0 0 0 42 57 1 0 0 0 0 42 59 1 0 0 0 0 43 4 1 6 0 0 0 44 5 1 6 0 0 0 45 13 1 6 0 0 0 45 46 1 0 0 0 0 45 62 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	883.49
Volume:	858.872
LogP:	1.445
LogD:	2.318
LogS:	-2.139
# Rotatable Bonds:	8
TPSA:	258.71
# H-Bond Aceptor:	17
# H-Bond Donor:	10
# Rings:	9
# Heavy Atoms:	17

MedChem Properties

QED Drug-Likeness Score:	0.142
Synthetic Accessibility Score:	6.761
Fsp3:	0.956
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:	-6.24
MDCK Permeability:	0.00025755504611879587
Pgp-inhibitor:	0.086
Pgp-substrate:	0.102
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	0.889
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178
Plasma Protein Binding (PPB):	33.490318298339844%
Volume Distribution (VD):	0.079
Pgp-substrate:	30.972564697265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.143
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.029

ADMET: Excretion

Clearance (CL):	0.673
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.659
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.166
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.796
Skin Sensitization:	0.046
Carcinogencity:	0.468
Eye Corrosion:	0.003
Eye Irritation:	0.002
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC150057

Natural Product ID:	NPC150057
*Common Name:**	QCTMYNGDIBTNSK-QOYYGLBOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QCTMYNGDIBTNSK-QOYYGLBOSA-N
Standard InCHI:	InChI=1S/C45H73NO16/c1-19-8-13-45(46-16-19)20(2)30-27(62-45)15-26-24-7-6-22-14-23(9-11-43(22,4)25(24)10-12-44(26,30)5)57-42-39(61-40-36(54)34(52)31(49)21(3)56-40)38(33(51)29(18-48)59-42)60-41-37(55)35(53)32(50)28(17-47)58-41/h6,19-21,23-42,46-55H,7-18H2,1-5H3/t19-,20-,21?,23-,24+,25-,26-,27-,28?,29?,30-,31?,32?,33?,34?,35?,36?,37?,38?,39?,40?,41?,42?,43-,44-,45+/m0/s1
SMILES:	OCC1OC(O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4C[C@H]4[C@@H]3[C@H](C)[C@]3(O4)CC[C@@H](CN3)C)C)C2)C)C(C(C1O)OC1OC(CO)C(C(C1O)O)O)OC1OC(C)C(C(C1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1967295
PubChem CID:	255983
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

*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
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	Whole plant	n.a.	steroidal saponins	PMID[16933867]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2211	Solanum nigrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2211	Solanum nigrum	Species	Solanaceae	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
GI50	57

Activity Type	# Activity
Cell Line	57

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	20749.14	nM	PMID[514203]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	20796.97	nM	PMID[514203]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	17579.24	nM	PMID[514203]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	18492.69	nM	PMID[514203]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	17538.81	nM	PMID[514203]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	19098.53	nM	PMID[514203]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	15452.54	nM	PMID[514203]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	19408.86	nM	PMID[514203]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	19186.69	nM	PMID[514203]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	16710.91	nM	PMID[514203]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	18030.18	nM	PMID[514203]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[514203]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	26915.35	nM	PMID[514203]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	18879.91	nM	PMID[514203]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	16368.17	nM	PMID[514203]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	15488.17	nM	PMID[514203]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	37153.52	nM	PMID[514203]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	14757.07	nM	PMID[514203]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	21379.62	nM	PMID[514203]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	20749.14	nM	PMID[514203]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	29040.23	nM	PMID[514203]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	17338.04	nM	PMID[514203]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	19186.69	nM	PMID[514203]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	20044.72	nM	PMID[514203]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	12823.31	nM	PMID[514203]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	19453.6	nM	PMID[514203]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	18365.38	nM	PMID[514203]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	19769.7	nM	PMID[514203]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	28313.92	nM	PMID[514203]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	17021.59	nM	PMID[514203]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	18407.72	nM	PMID[514203]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	18281.0	nM	PMID[514203]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	18113.4	nM	PMID[514203]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	14487.72	nM	PMID[514203]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	20090.93	nM	PMID[514203]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	16710.91	nM	PMID[514203]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	16519.62	nM	PMID[514203]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	16634.13	nM	PMID[514203]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	16865.53	nM	PMID[514203]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	18071.74	nM	PMID[514203]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	16865.53	nM	PMID[514203]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	17782.79	nM	PMID[514203]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	19543.39	nM	PMID[514203]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	17619.76	nM	PMID[514203]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	19186.69	nM	PMID[514203]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	18407.72	nM	PMID[514203]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	23496.33	nM	PMID[514203]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	19498.45	nM	PMID[514203]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	23988.33	nM	PMID[514203]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	14689.26	nM	PMID[514203]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	18155.16	nM	PMID[514203]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	21577.44	nM	PMID[514203]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	17782.79	nM	PMID[514203]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	17418.07	nM	PMID[514203]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	15776.11	nM	PMID[514203]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	19054.61	nM	PMID[514203]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	17947.34	nM	PMID[514203]

☑ 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 NPC150057 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	171
0.1-0.2	1262
0.2-0.3	10329
0.3-0.4	15301
0.4-0.5	9124
0.5-0.6	4135
0.6-0.7	1735
0.7-0.8	538
0.8-0.85	91
0.85-0.9	4
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC147753
0.9918	High Similarity	NPC122819
0.9836	High Similarity	NPC15249
0.9836	High Similarity	NPC25455
0.9683	High Similarity	NPC287885
0.9187	High Similarity	NPC296686
0.8661	High Similarity	NPC94881
0.8661	High Similarity	NPC265275
0.8661	High Similarity	NPC48886
0.8358	Intermediate Similarity	NPC297058
0.8197	Intermediate Similarity	NPC46190
0.8197	Intermediate Similarity	NPC224098
0.8197	Intermediate Similarity	NPC147835
0.8197	Intermediate Similarity	NPC85001
0.8197	Intermediate Similarity	NPC150372
0.8197	Intermediate Similarity	NPC232054
0.8197	Intermediate Similarity	NPC171073
0.8197	Intermediate Similarity	NPC6806
0.8197	Intermediate Similarity	NPC475550
0.8197	Intermediate Similarity	NPC95051
0.8197	Intermediate Similarity	NPC300557
0.8197	Intermediate Similarity	NPC309278
0.8197	Intermediate Similarity	NPC248746
0.8197	Intermediate Similarity	NPC218571
0.8197	Intermediate Similarity	NPC249265
0.8197	Intermediate Similarity	NPC194207
0.8197	Intermediate Similarity	NPC95920
0.8197	Intermediate Similarity	NPC470433
0.8197	Intermediate Similarity	NPC475333
0.8197	Intermediate Similarity	NPC22779
0.8197	Intermediate Similarity	NPC84956
0.8197	Intermediate Similarity	NPC244086
0.8197	Intermediate Similarity	NPC102016
0.8197	Intermediate Similarity	NPC253645
0.8197	Intermediate Similarity	NPC477809
0.8197	Intermediate Similarity	NPC73243
0.8197	Intermediate Similarity	NPC208383
0.813	Intermediate Similarity	NPC23808
0.813	Intermediate Similarity	NPC222202
0.813	Intermediate Similarity	NPC87998
0.813	Intermediate Similarity	NPC477811
0.813	Intermediate Similarity	NPC269297
0.813	Intermediate Similarity	NPC224314
0.8115	Intermediate Similarity	NPC98696
0.8065	Intermediate Similarity	NPC124677
0.8065	Intermediate Similarity	NPC477028
0.8065	Intermediate Similarity	NPC294129
0.8065	Intermediate Similarity	NPC477032
0.8065	Intermediate Similarity	NPC476547
0.8065	Intermediate Similarity	NPC475247
0.8065	Intermediate Similarity	NPC13193
0.8033	Intermediate Similarity	NPC94272
0.8033	Intermediate Similarity	NPC14704
0.8033	Intermediate Similarity	NPC230507
0.8033	Intermediate Similarity	NPC470432
0.8033	Intermediate Similarity	NPC305423
0.8033	Intermediate Similarity	NPC283829
0.8033	Intermediate Similarity	NPC113044
0.8033	Intermediate Similarity	NPC161676
0.8	Intermediate Similarity	NPC244431
0.8	Intermediate Similarity	NPC31896
0.8	Intermediate Similarity	NPC210569
0.8	Intermediate Similarity	NPC42171
0.8	Intermediate Similarity	NPC32361
0.8	Intermediate Similarity	NPC262050
0.8	Intermediate Similarity	NPC263359
0.7984	Intermediate Similarity	NPC247037
0.7951	Intermediate Similarity	NPC181845
0.7937	Intermediate Similarity	NPC79900
0.7903	Intermediate Similarity	NPC42482
0.7903	Intermediate Similarity	NPC475670
0.7903	Intermediate Similarity	NPC477026
0.7903	Intermediate Similarity	NPC40440
0.7903	Intermediate Similarity	NPC477027
0.7903	Intermediate Similarity	NPC306131
0.7903	Intermediate Similarity	NPC70204
0.7874	Intermediate Similarity	NPC167183
0.7874	Intermediate Similarity	NPC32707
0.7874	Intermediate Similarity	NPC477810
0.7874	Intermediate Similarity	NPC11548
0.7874	Intermediate Similarity	NPC477808
0.7857	Intermediate Similarity	NPC308140
0.7857	Intermediate Similarity	NPC254255
0.784	Intermediate Similarity	NPC141433
0.7823	Intermediate Similarity	NPC476540
0.7823	Intermediate Similarity	NPC476538
0.7823	Intermediate Similarity	NPC476539
0.7823	Intermediate Similarity	NPC476541
0.7812	Intermediate Similarity	NPC477030
0.7812	Intermediate Similarity	NPC477029
0.7812	Intermediate Similarity	NPC63609
0.7812	Intermediate Similarity	NPC477031
0.7795	Intermediate Similarity	NPC476546
0.7778	Intermediate Similarity	NPC197231
0.7752	Intermediate Similarity	NPC477807
0.7734	Intermediate Similarity	NPC208832
0.7717	Intermediate Similarity	NPC112274
0.7717	Intermediate Similarity	NPC19888
0.7661	Intermediate Similarity	NPC242748
0.7661	Intermediate Similarity	NPC473476
0.7661	Intermediate Similarity	NPC309448
0.7661	Intermediate Similarity	NPC473923
0.7661	Intermediate Similarity	NPC474569
0.7656	Intermediate Similarity	NPC476693
0.7656	Intermediate Similarity	NPC469348
0.7656	Intermediate Similarity	NPC307642
0.7656	Intermediate Similarity	NPC469347
0.7656	Intermediate Similarity	NPC51154
0.7638	Intermediate Similarity	NPC13190
0.7638	Intermediate Similarity	NPC470748
0.7634	Intermediate Similarity	NPC195560
0.7634	Intermediate Similarity	NPC229962
0.7619	Intermediate Similarity	NPC302057
0.76	Intermediate Similarity	NPC190395
0.76	Intermediate Similarity	NPC226642
0.7581	Intermediate Similarity	NPC212874
0.7576	Intermediate Similarity	NPC207243
0.7576	Intermediate Similarity	NPC50689
0.7576	Intermediate Similarity	NPC198325
0.7576	Intermediate Similarity	NPC233391
0.7561	Intermediate Similarity	NPC272015
0.7561	Intermediate Similarity	NPC176012
0.7557	Intermediate Similarity	NPC475357
0.754	Intermediate Similarity	NPC220427
0.754	Intermediate Similarity	NPC295980
0.7538	Intermediate Similarity	NPC148965
0.752	Intermediate Similarity	NPC26798
0.7519	Intermediate Similarity	NPC476545
0.7519	Intermediate Similarity	NPC476543
0.7519	Intermediate Similarity	NPC249553
0.7519	Intermediate Similarity	NPC476544
0.7519	Intermediate Similarity	NPC182900
0.7519	Intermediate Similarity	NPC476671
0.75	Intermediate Similarity	NPC473633
0.75	Intermediate Similarity	NPC476085
0.7481	Intermediate Similarity	NPC20979
0.748	Intermediate Similarity	NPC476835
0.7463	Intermediate Similarity	NPC469943
0.7463	Intermediate Similarity	NPC169816
0.7463	Intermediate Similarity	NPC15918
0.7463	Intermediate Similarity	NPC94072
0.7463	Intermediate Similarity	NPC43842
0.7463	Intermediate Similarity	NPC305771
0.746	Intermediate Similarity	NPC208650
0.746	Intermediate Similarity	NPC473469
0.746	Intermediate Similarity	NPC14946
0.746	Intermediate Similarity	NPC63368
0.744	Intermediate Similarity	NPC187400
0.744	Intermediate Similarity	NPC470885
0.744	Intermediate Similarity	NPC221562
0.7424	Intermediate Similarity	NPC475403
0.7424	Intermediate Similarity	NPC476691
0.7424	Intermediate Similarity	NPC10366
0.7424	Intermediate Similarity	NPC160888
0.7424	Intermediate Similarity	NPC476692
0.7407	Intermediate Similarity	NPC106589
0.7407	Intermediate Similarity	NPC257207
0.7407	Intermediate Similarity	NPC202261
0.7407	Intermediate Similarity	NPC295133
0.7407	Intermediate Similarity	NPC256983
0.7402	Intermediate Similarity	NPC125324
0.7402	Intermediate Similarity	NPC159005
0.7402	Intermediate Similarity	NPC246124
0.7402	Intermediate Similarity	NPC7213
0.7402	Intermediate Similarity	NPC180183
0.7402	Intermediate Similarity	NPC51172
0.7402	Intermediate Similarity	NPC49032
0.7402	Intermediate Similarity	NPC6931
0.7402	Intermediate Similarity	NPC128123
0.7398	Intermediate Similarity	NPC282669
0.7385	Intermediate Similarity	NPC144068
0.7381	Intermediate Similarity	NPC208594
0.7381	Intermediate Similarity	NPC269627
0.7381	Intermediate Similarity	NPC160816
0.7381	Intermediate Similarity	NPC69737
0.7381	Intermediate Similarity	NPC208477
0.7381	Intermediate Similarity	NPC127801
0.7381	Intermediate Similarity	NPC152584
0.7381	Intermediate Similarity	NPC194842
0.7377	Intermediate Similarity	NPC473890
0.7377	Intermediate Similarity	NPC243728
0.7368	Intermediate Similarity	NPC161738
0.7364	Intermediate Similarity	NPC92710
0.7364	Intermediate Similarity	NPC114188
0.7348	Intermediate Similarity	NPC100048
0.7348	Intermediate Similarity	NPC476690
0.7344	Intermediate Similarity	NPC157530
0.7344	Intermediate Similarity	NPC14630
0.7344	Intermediate Similarity	NPC151134
0.7344	Intermediate Similarity	NPC250089
0.7333	Intermediate Similarity	NPC478138
0.7323	Intermediate Similarity	NPC181467
0.7317	Intermediate Similarity	NPC158088
0.7313	Intermediate Similarity	NPC473566
0.7313	Intermediate Similarity	NPC475358
0.7302	Intermediate Similarity	NPC475365
0.7292	Intermediate Similarity	NPC302276
0.7287	Intermediate Similarity	NPC470867
0.728	Intermediate Similarity	NPC288694
0.728	Intermediate Similarity	NPC159036

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 NPC150057 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	114
0.1-0.2	793
0.2-0.3	4248
0.3-0.4	2985
0.4-0.5	754
0.5-0.6	213
0.6-0.7	32
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8450	Suspended
0.9918	High Similarity	NPD8449	Approved
0.6934	Remote Similarity	NPD8294	Approved
0.6934	Remote Similarity	NPD8377	Approved
0.6917	Remote Similarity	NPD6430	Approved
0.6917	Remote Similarity	NPD6429	Approved
0.6884	Remote Similarity	NPD8296	Approved
0.6884	Remote Similarity	NPD8379	Approved
0.6884	Remote Similarity	NPD8335	Approved
0.6884	Remote Similarity	NPD8033	Approved
0.6884	Remote Similarity	NPD8380	Approved
0.6884	Remote Similarity	NPD8378	Approved
0.6774	Remote Similarity	NPD8171	Discontinued
0.6667	Remote Similarity	NPD6412	Phase 2
0.6547	Remote Similarity	NPD7328	Approved
0.6547	Remote Similarity	NPD7327	Approved
0.65	Remote Similarity	NPD7516	Approved
0.6496	Remote Similarity	NPD8133	Approved
0.6408	Remote Similarity	NPD7503	Approved
0.6406	Remote Similarity	NPD7991	Discontinued
0.637	Remote Similarity	NPD8337	Approved
0.637	Remote Similarity	NPD8336	Approved
0.6269	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD7507	Approved
0.6203	Remote Similarity	NPD7625	Phase 1
0.6149	Remote Similarity	NPD7736	Approved
0.6138	Remote Similarity	NPD6370	Approved
0.6131	Remote Similarity	NPD8174	Phase 2
0.6107	Remote Similarity	NPD7319	Approved
0.6096	Remote Similarity	NPD8328	Phase 3
0.6087	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD8293	Discontinued
0.6071	Remote Similarity	NPD7335	Phase 2
0.6071	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD7336	Phase 2
0.6056	Remote Similarity	NPD6940	Discontinued
0.6014	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8345	Approved
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD8347	Approved
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD8346	Approved
0.5987	Remote Similarity	NPD8338	Approved
0.5959	Remote Similarity	NPD8267	Approved
0.5959	Remote Similarity	NPD8268	Approved
0.5959	Remote Similarity	NPD8269	Approved
0.5959	Remote Similarity	NPD8266	Approved
0.5944	Remote Similarity	NPD4831	Approved
0.5944	Remote Similarity	NPD4830	Approved
0.5944	Remote Similarity	NPD7754	Approved
0.5944	Remote Similarity	NPD7755	Approved
0.5944	Remote Similarity	NPD4832	Approved
0.5915	Remote Similarity	NPD3731	Phase 3
0.5903	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD6686	Approved
0.5878	Remote Similarity	NPD7122	Discontinued
0.5878	Remote Similarity	NPD6067	Discontinued
0.5855	Remote Similarity	NPD6914	Discontinued
0.585	Remote Similarity	NPD8516	Approved
0.585	Remote Similarity	NPD6015	Approved
0.585	Remote Similarity	NPD6016	Approved
0.585	Remote Similarity	NPD8515	Approved
0.585	Remote Similarity	NPD8517	Approved
0.5839	Remote Similarity	NPD7492	Approved
0.5811	Remote Similarity	NPD5988	Approved
0.5811	Remote Similarity	NPD6436	Phase 3
0.5806	Remote Similarity	NPD6928	Phase 2
0.58	Remote Similarity	NPD6616	Approved
0.5781	Remote Similarity	NPD8308	Discontinued
0.5762	Remote Similarity	NPD7078	Approved
0.5755	Remote Similarity	NPD7333	Discontinued
0.5752	Remote Similarity	NPD8391	Approved
0.5752	Remote Similarity	NPD8390	Approved
0.5752	Remote Similarity	NPD8392	Approved
0.5743	Remote Similarity	NPD6909	Approved
0.5743	Remote Similarity	NPD8513	Phase 3
0.5743	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6908	Approved
0.5738	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD7524	Approved
0.5733	Remote Similarity	NPD591	Approved
0.5733	Remote Similarity	NPD577	Phase 3
0.5667	Remote Similarity	NPD7829	Approved
0.5667	Remote Similarity	NPD7830	Approved
0.5664	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD8448	Approved
0.5656	Remote Similarity	NPD7339	Approved
0.5656	Remote Similarity	NPD6942	Approved
0.5643	Remote Similarity	NPD5357	Phase 1
0.5638	Remote Similarity	NPD8444	Approved
0.5629	Remote Similarity	NPD8299	Approved
0.5629	Remote Similarity	NPD8341	Approved
0.5629	Remote Similarity	NPD8340	Approved
0.5629	Remote Similarity	NPD8342	Approved
0.5625	Remote Similarity	NPD6882	Approved
0.5625	Remote Similarity	NPD8078	Approved
0.5625	Remote Similarity	NPD8077	Approved
0.5625	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD8297	Approved
0.5621	Remote Similarity	NPD6033	Approved
0.5615	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5603	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.56	Remote Similarity	NPD8080	Discontinued

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