NPASS Compound

Structure

CID277191 OpenBabel06191716082D 48 54 0 0 1 0 0 0 0 0999 V2000 -1.8986 0.9215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9579 -1.0979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8219 -0.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2070 6.7417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0629 6.2473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8703 4.8162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8695 1.8763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3945 3.3325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5390 5.7535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7046 5.2721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2062 3.8266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2028 3.8280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7038 2.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5034 1.3261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3476 0.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0346 1.4214 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3730 5.2717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3727 4.3085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0399 4.3080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2026 2.8654 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4661 1.3258 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7044 4.3089 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5381 2.8645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0354 2.3836 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9472 0.4920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9099 0.4917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3915 1.3253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0402 5.2712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9104 2.1592 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9570 -0.0997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2067 5.7530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8700 3.8276 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8698 2.8650 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5384 3.8271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6320 1.4228 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2009 0.9410 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0218 0.4925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3886 2.3732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4656 -0.3417 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3911 -0.3422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3542 1.3251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8910 5.7619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2180 2.2309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1935 0.8358 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8735 3.8264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9477 2.1594 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6312 2.3851 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 16 1 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 9 10 1 0 0 0 0 9 17 2 0 0 0 0 10 22 1 0 0 0 0 11 18 1 0 0 0 0 11 19 2 0 0 0 0 12 32 1 0 0 0 0 13 23 1 0 0 0 0 13 33 1 0 0 0 0 14 37 1 0 0 0 0 15 30 1 0 0 0 0 15 35 1 0 0 0 0 16 24 1 0 0 0 0 16 36 1 1 0 0 0 17 18 1 0 0 0 0 17 31 1 0 0 0 0 18 34 1 6 0 0 0 19 28 1 0 0 0 0 19 45 1 0 0 0 0 20 12 1 1 0 0 0 20 24 1 0 0 0 0 20 47 1 0 0 0 0 21 14 1 6 0 0 0 21 25 1 0 0 0 0 21 46 1 0 0 0 0 22 32 1 1 0 0 0 22 34 1 0 0 0 0 23 34 1 0 0 0 0 23 38 2 0 0 0 0 24 33 1 6 0 0 0 25 26 1 0 0 0 0 25 39 1 1 0 0 0 26 27 1 0 0 0 0 26 40 1 6 0 0 0 27 29 1 0 0 0 0 27 41 1 1 0 0 0 28 31 1 0 0 0 0 28 42 2 0 0 0 0 29 45 1 6 0 0 0 29 46 1 0 0 0 0 30 48 1 0 0 0 0 32 33 1 1 0 0 0 33 7 1 6 0 0 0 34 8 1 6 0 0 0 35 36 1 6 0 0 0 35 43 1 0 0 0 0 35 47 1 0 0 0 0 36 44 1 6 0 0 0 36 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	676.35
Volume:	666.254
LogP:	2.366
LogD:	2.136
LogS:	-4.076
# Rotatable Bonds:	3
TPSA:	192.44
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	6.218
Fsp3:	0.833
Lipinski Rule-of-5:	Rejected
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:	-5.208
MDCK Permeability:	2.1948382709524594e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.482
20% Bioavailability (F20%):	0.907
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	77.3216323852539%
Volume Distribution (VD):	0.813
Pgp-substrate:	13.395689010620117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.381
CYP3A4-substrate:	0.548

ADMET: Excretion

Clearance (CL):	3.799
Half-life (T1/2):	0.662

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.31
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.167
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.027
Carcinogencity:	0.876
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC277191

Natural Product ID:	NPC277191
*Common Name:**	ACPPAFATSKFQFS-YTBYLDSSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ACPPAFATSKFQFS-YTBYLDSSSA-N
Standard InCHI:	InChI=1S/C36H52O12/c1-16-24-20(47-35(43)15-30(2,3)48-36(16,35)44)12-32(6)22-10-9-17-18(34(22,8)23(38)13-33(24,32)7)11-19(28(42)31(17,4)5)45-29-27(41)26(40)25(39)21(14-37)46-29/h9,11,16,18,20-22,24-27,29,37,39-41,43-44H,10,12-15H2,1-8H3/t16-,18+,20+,21+,22-,24-,25+,26-,27+,29+,32-,33+,34-,35-,36-/m0/s1
SMILES:	OC[C@H]1O[C@@H](OC2=C[C@@H]3C(=CC[C@@H]4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)C[C@@H]4[C@@H]3[C@H](C)[C@]3([C@](O4)(O)CC(O3)(C)C)O)C)C(C2=O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923780
PubChem CID:	56833654
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[22044245]
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	root	Dayao Mountain, Guangxi, China	2007-DEC	PMID[22044245]
NPO30742	Machilus yaoshansis	Species	Lauraceae	Eukaryota	Roots	n.a.	n.a.	PMID[22779787]

☑ 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	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[471427]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[471427]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[471427]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[471427]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[471427]

☑ 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 NPC277191 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	287
0.1-0.2	1673
0.2-0.3	5688
0.3-0.4	10859
0.4-0.5	10110
0.5-0.6	7179
0.6-0.7	4568
0.7-0.8	2190
0.8-0.85	104
0.85-0.9	30
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC190846
0.9565	High Similarity	NPC42675
0.9407	High Similarity	NPC93368
0.9402	High Similarity	NPC141196
0.9402	High Similarity	NPC238005
0.9402	High Similarity	NPC1980
0.925	High Similarity	NPC69273
0.925	High Similarity	NPC293623
0.925	High Similarity	NPC168899
0.9244	High Similarity	NPC198714
0.9167	High Similarity	NPC152091
0.9153	High Similarity	NPC216866
0.9098	High Similarity	NPC241008
0.9	High Similarity	NPC475194
0.8943	High Similarity	NPC213634
0.8833	High Similarity	NPC131824
0.8803	High Similarity	NPC31797
0.8793	High Similarity	NPC477944
0.876	High Similarity	NPC476542
0.876	High Similarity	NPC228701
0.875	High Similarity	NPC476543
0.875	High Similarity	NPC476544
0.875	High Similarity	NPC476545
0.8739	High Similarity	NPC161738
0.8689	High Similarity	NPC473505
0.8689	High Similarity	NPC6615
0.8689	High Similarity	NPC7850
0.8678	High Similarity	NPC475431
0.8655	High Similarity	NPC176005
0.8618	High Similarity	NPC104427
0.8595	High Similarity	NPC249553
0.8595	High Similarity	NPC182900
0.8583	High Similarity	NPC473920
0.8583	High Similarity	NPC319570
0.8559	High Similarity	NPC474557
0.8548	High Similarity	NPC292290
0.8548	High Similarity	NPC2757
0.8537	High Similarity	NPC177820
0.8537	High Similarity	NPC30188
0.8525	High Similarity	NPC15918
0.8525	High Similarity	NPC169816
0.8525	High Similarity	NPC94072
0.8525	High Similarity	NPC305771
0.8475	Intermediate Similarity	NPC260665
0.8455	Intermediate Similarity	NPC227397
0.8448	Intermediate Similarity	NPC246205
0.8443	Intermediate Similarity	NPC278163
0.8443	Intermediate Similarity	NPC187950
0.843	Intermediate Similarity	NPC279143
0.8403	Intermediate Similarity	NPC471398
0.8403	Intermediate Similarity	NPC165439
0.839	Intermediate Similarity	NPC474265
0.839	Intermediate Similarity	NPC130427
0.839	Intermediate Similarity	NPC210420
0.8387	Intermediate Similarity	NPC469842
0.8387	Intermediate Similarity	NPC469841
0.8376	Intermediate Similarity	NPC27551
0.8376	Intermediate Similarity	NPC114961
0.8374	Intermediate Similarity	NPC28532
0.8362	Intermediate Similarity	NPC473288
0.8359	Intermediate Similarity	NPC475487
0.8348	Intermediate Similarity	NPC63023
0.8348	Intermediate Similarity	NPC95243
0.8347	Intermediate Similarity	NPC475632
0.8347	Intermediate Similarity	NPC86020
0.8346	Intermediate Similarity	NPC803
0.832	Intermediate Similarity	NPC47113
0.832	Intermediate Similarity	NPC174367
0.8319	Intermediate Similarity	NPC178981
0.8319	Intermediate Similarity	NPC73455
0.8319	Intermediate Similarity	NPC200944
0.8293	Intermediate Similarity	NPC275675
0.8293	Intermediate Similarity	NPC133506
0.8293	Intermediate Similarity	NPC202051
0.8291	Intermediate Similarity	NPC304495
0.8291	Intermediate Similarity	NPC470257
0.8281	Intermediate Similarity	NPC471855
0.8279	Intermediate Similarity	NPC127530
0.8268	Intermediate Similarity	NPC309096
0.8268	Intermediate Similarity	NPC54614
0.8261	Intermediate Similarity	NPC100955
0.8261	Intermediate Similarity	NPC121566
0.8254	Intermediate Similarity	NPC329784
0.8254	Intermediate Similarity	NPC240070
0.825	Intermediate Similarity	NPC473882
0.825	Intermediate Similarity	NPC477580
0.825	Intermediate Similarity	NPC74727
0.824	Intermediate Similarity	NPC130229
0.822	Intermediate Similarity	NPC163314
0.822	Intermediate Similarity	NPC154856
0.822	Intermediate Similarity	NPC52241
0.822	Intermediate Similarity	NPC475317
0.8211	Intermediate Similarity	NPC471406
0.8211	Intermediate Similarity	NPC475187
0.819	Intermediate Similarity	NPC162033
0.819	Intermediate Similarity	NPC210178
0.8189	Intermediate Similarity	NPC475636
0.8189	Intermediate Similarity	NPC295220
0.8182	Intermediate Similarity	NPC279638
0.8175	Intermediate Similarity	NPC285091
0.8168	Intermediate Similarity	NPC127656
0.8168	Intermediate Similarity	NPC141215
0.8168	Intermediate Similarity	NPC190065
0.8168	Intermediate Similarity	NPC471089
0.8167	Intermediate Similarity	NPC251309
0.8167	Intermediate Similarity	NPC194100
0.8154	Intermediate Similarity	NPC478069
0.8145	Intermediate Similarity	NPC475182
0.8145	Intermediate Similarity	NPC241310
0.8145	Intermediate Similarity	NPC131841
0.8145	Intermediate Similarity	NPC194310
0.8145	Intermediate Similarity	NPC412
0.8145	Intermediate Similarity	NPC258789
0.8145	Intermediate Similarity	NPC258815
0.8145	Intermediate Similarity	NPC169727
0.8145	Intermediate Similarity	NPC47567
0.814	Intermediate Similarity	NPC155529
0.814	Intermediate Similarity	NPC473805
0.814	Intermediate Similarity	NPC473519
0.8136	Intermediate Similarity	NPC118225
0.813	Intermediate Similarity	NPC190939
0.813	Intermediate Similarity	NPC197003
0.8125	Intermediate Similarity	NPC276838
0.8125	Intermediate Similarity	NPC329986
0.8125	Intermediate Similarity	NPC140092
0.8125	Intermediate Similarity	NPC232785
0.8125	Intermediate Similarity	NPC188234
0.8125	Intermediate Similarity	NPC125077
0.8125	Intermediate Similarity	NPC471407
0.812	Intermediate Similarity	NPC58370
0.812	Intermediate Similarity	NPC43285
0.8115	Intermediate Similarity	NPC309433
0.811	Intermediate Similarity	NPC305496
0.8106	Intermediate Similarity	NPC295885
0.8106	Intermediate Similarity	NPC596
0.8106	Intermediate Similarity	NPC140045
0.8103	Intermediate Similarity	NPC223741
0.8092	Intermediate Similarity	NPC262813
0.8092	Intermediate Similarity	NPC158350
0.8083	Intermediate Similarity	NPC233003
0.808	Intermediate Similarity	NPC313528
0.808	Intermediate Similarity	NPC156789
0.808	Intermediate Similarity	NPC471965
0.8077	Intermediate Similarity	NPC102015
0.8067	Intermediate Similarity	NPC129340
0.8065	Intermediate Similarity	NPC170814
0.8065	Intermediate Similarity	NPC308459
0.8062	Intermediate Similarity	NPC173347
0.8051	Intermediate Similarity	NPC272576
0.8047	Intermediate Similarity	NPC311534
0.8047	Intermediate Similarity	NPC245094
0.8045	Intermediate Similarity	NPC290746
0.8045	Intermediate Similarity	NPC79250
0.8034	Intermediate Similarity	NPC181845
0.8033	Intermediate Similarity	NPC235539
0.8033	Intermediate Similarity	NPC152199
0.8033	Intermediate Similarity	NPC189126
0.8033	Intermediate Similarity	NPC134869
0.8031	Intermediate Similarity	NPC87662
0.803	Intermediate Similarity	NPC251998
0.8017	Intermediate Similarity	NPC471627
0.8017	Intermediate Similarity	NPC293038
0.8017	Intermediate Similarity	NPC62696
0.8017	Intermediate Similarity	NPC471173
0.8016	Intermediate Similarity	NPC27363
0.8016	Intermediate Similarity	NPC14617
0.8016	Intermediate Similarity	NPC471961
0.8016	Intermediate Similarity	NPC160084
0.8016	Intermediate Similarity	NPC262199
0.8016	Intermediate Similarity	NPC471964
0.8016	Intermediate Similarity	NPC202666
0.8016	Intermediate Similarity	NPC256983
0.8	Intermediate Similarity	NPC476675
0.8	Intermediate Similarity	NPC476672
0.8	Intermediate Similarity	NPC477073
0.8	Intermediate Similarity	NPC274833
0.7984	Intermediate Similarity	NPC258592
0.7984	Intermediate Similarity	NPC178548
0.7983	Intermediate Similarity	NPC42482
0.7983	Intermediate Similarity	NPC265655
0.7983	Intermediate Similarity	NPC40440
0.7982	Intermediate Similarity	NPC56071
0.7982	Intermediate Similarity	NPC70733
0.7966	Intermediate Similarity	NPC470432
0.7966	Intermediate Similarity	NPC113044
0.7966	Intermediate Similarity	NPC161676
0.7966	Intermediate Similarity	NPC305423
0.7966	Intermediate Similarity	NPC14704
0.7966	Intermediate Similarity	NPC283829
0.7966	Intermediate Similarity	NPC230507
0.7955	Intermediate Similarity	NPC171619
0.7953	Intermediate Similarity	NPC476674
0.7953	Intermediate Similarity	NPC473474
0.7953	Intermediate Similarity	NPC471963
0.7953	Intermediate Similarity	NPC247315
0.7953	Intermediate Similarity	NPC248202
0.7953	Intermediate Similarity	NPC318135
0.7953	Intermediate Similarity	NPC471962
0.7951	Intermediate Similarity	NPC18547
0.7951	Intermediate Similarity	NPC116024

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 NPC277191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	1911
0.2-0.3	4229
0.3-0.4	1805
0.4-0.5	482
0.5-0.6	247
0.6-0.7	131
0.7-0.8	85
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8525	High Similarity	NPD6370	Approved
0.848	Intermediate Similarity	NPD7736	Approved
0.8435	Intermediate Similarity	NPD6412	Phase 2
0.8361	Intermediate Similarity	NPD6054	Approved
0.8254	Intermediate Similarity	NPD8293	Discontinued
0.8211	Intermediate Similarity	NPD6059	Approved
0.8145	Intermediate Similarity	NPD6016	Approved
0.8145	Intermediate Similarity	NPD6015	Approved
0.8095	Intermediate Similarity	NPD7492	Approved
0.808	Intermediate Similarity	NPD5988	Approved
0.8031	Intermediate Similarity	NPD6616	Approved
0.8016	Intermediate Similarity	NPD8328	Phase 3
0.7969	Intermediate Similarity	NPD7078	Approved
0.7934	Intermediate Similarity	NPD8297	Approved
0.7934	Intermediate Similarity	NPD6882	Approved
0.7891	Intermediate Similarity	NPD7507	Approved
0.7823	Intermediate Similarity	NPD6009	Approved
0.7778	Intermediate Similarity	NPD6319	Approved
0.7717	Intermediate Similarity	NPD7503	Approved
0.771	Intermediate Similarity	NPD7319	Approved
0.7647	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD8294	Approved
0.7638	Intermediate Similarity	NPD8377	Approved
0.7634	Intermediate Similarity	NPD6033	Approved
0.7603	Intermediate Similarity	NPD6881	Approved
0.7603	Intermediate Similarity	NPD6899	Approved
0.7603	Intermediate Similarity	NPD7320	Approved
0.7583	Intermediate Similarity	NPD6675	Approved
0.7583	Intermediate Similarity	NPD6402	Approved
0.7583	Intermediate Similarity	NPD7128	Approved
0.7583	Intermediate Similarity	NPD5739	Approved
0.7581	Intermediate Similarity	NPD4632	Approved
0.7578	Intermediate Similarity	NPD8296	Approved
0.7578	Intermediate Similarity	NPD8380	Approved
0.7578	Intermediate Similarity	NPD8335	Approved
0.7578	Intermediate Similarity	NPD8379	Approved
0.7578	Intermediate Similarity	NPD8378	Approved
0.7578	Intermediate Similarity	NPD8033	Approved
0.7561	Intermediate Similarity	NPD8130	Phase 1
0.7561	Intermediate Similarity	NPD6649	Approved
0.7561	Intermediate Similarity	NPD6650	Approved
0.7541	Intermediate Similarity	NPD6372	Approved
0.7541	Intermediate Similarity	NPD6373	Approved
0.754	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD5697	Approved
0.748	Intermediate Similarity	NPD7102	Approved
0.748	Intermediate Similarity	NPD6883	Approved
0.748	Intermediate Similarity	NPD7290	Approved
0.7459	Intermediate Similarity	NPD6686	Approved
0.744	Intermediate Similarity	NPD8133	Approved
0.7436	Intermediate Similarity	NPD6084	Phase 2
0.7436	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD6869	Approved
0.7419	Intermediate Similarity	NPD6617	Approved
0.7419	Intermediate Similarity	NPD6847	Approved
0.7414	Intermediate Similarity	NPD5695	Phase 3
0.7398	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6013	Approved
0.7398	Intermediate Similarity	NPD6012	Approved
0.7398	Intermediate Similarity	NPD6014	Approved
0.7388	Intermediate Similarity	NPD5956	Approved
0.7377	Intermediate Similarity	NPD5701	Approved
0.7344	Intermediate Similarity	NPD7328	Approved
0.7344	Intermediate Similarity	NPD7327	Approved
0.7339	Intermediate Similarity	NPD4634	Approved
0.7328	Intermediate Similarity	NPD7604	Phase 2
0.7317	Intermediate Similarity	NPD6011	Approved
0.7311	Intermediate Similarity	NPD4696	Approved
0.7311	Intermediate Similarity	NPD5286	Approved
0.7311	Intermediate Similarity	NPD5285	Approved
0.7308	Intermediate Similarity	NPD5983	Phase 2
0.7288	Intermediate Similarity	NPD4755	Approved
0.7287	Intermediate Similarity	NPD7516	Approved
0.7218	Intermediate Similarity	NPD6336	Discontinued
0.7197	Intermediate Similarity	NPD6067	Discontinued
0.719	Intermediate Similarity	NPD5225	Approved
0.719	Intermediate Similarity	NPD4633	Approved
0.719	Intermediate Similarity	NPD5224	Approved
0.719	Intermediate Similarity	NPD5226	Approved
0.719	Intermediate Similarity	NPD5211	Phase 2
0.7167	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD5175	Approved
0.7131	Intermediate Similarity	NPD5174	Approved
0.713	Intermediate Similarity	NPD4753	Phase 2
0.7107	Intermediate Similarity	NPD5223	Approved
0.7087	Intermediate Similarity	NPD6053	Discontinued
0.7083	Intermediate Similarity	NPD5696	Approved
0.7073	Intermediate Similarity	NPD5141	Approved
0.7054	Intermediate Similarity	NPD6274	Approved
0.704	Intermediate Similarity	NPD4729	Approved
0.704	Intermediate Similarity	NPD4730	Approved
0.7023	Intermediate Similarity	NPD7100	Approved
0.7023	Intermediate Similarity	NPD7101	Approved
0.7016	Intermediate Similarity	NPD4767	Approved
0.7016	Intermediate Similarity	NPD4768	Approved
0.7016	Intermediate Similarity	NPD6008	Approved
0.6975	Remote Similarity	NPD4629	Approved
0.6975	Remote Similarity	NPD5210	Approved
0.6947	Remote Similarity	NPD6335	Approved
0.6929	Remote Similarity	NPD5247	Approved
0.6929	Remote Similarity	NPD5250	Approved
0.6929	Remote Similarity	NPD5249	Phase 3
0.6929	Remote Similarity	NPD5251	Approved
0.6929	Remote Similarity	NPD5248	Approved
0.6917	Remote Similarity	NPD8515	Approved
0.6917	Remote Similarity	NPD8516	Approved
0.6917	Remote Similarity	NPD8517	Approved
0.6917	Remote Similarity	NPD8513	Phase 3
0.6905	Remote Similarity	NPD5128	Approved
0.6875	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5690	Phase 2
0.687	Remote Similarity	NPD6317	Approved
0.6864	Remote Similarity	NPD6050	Approved
0.6861	Remote Similarity	NPD8336	Approved
0.6861	Remote Similarity	NPD8337	Approved
0.6855	Remote Similarity	NPD4754	Approved
0.6838	Remote Similarity	NPD6673	Approved
0.6838	Remote Similarity	NPD6904	Approved
0.6838	Remote Similarity	NPD6080	Approved
0.6818	Remote Similarity	NPD6314	Approved
0.6818	Remote Similarity	NPD6313	Approved
0.6807	Remote Similarity	NPD8171	Discontinued
0.6791	Remote Similarity	NPD6909	Approved
0.6791	Remote Similarity	NPD6908	Approved
0.6791	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5329	Approved
0.678	Remote Similarity	NPD5692	Phase 3
0.6777	Remote Similarity	NPD5221	Approved
0.6777	Remote Similarity	NPD5222	Approved
0.6777	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6672	Approved
0.6752	Remote Similarity	NPD5737	Approved
0.675	Remote Similarity	NPD5282	Discontinued
0.6744	Remote Similarity	NPD5217	Approved
0.6744	Remote Similarity	NPD5215	Approved
0.6744	Remote Similarity	NPD5216	Approved
0.6741	Remote Similarity	NPD8080	Discontinued
0.6724	Remote Similarity	NPD4694	Approved
0.6724	Remote Similarity	NPD5279	Phase 3
0.6724	Remote Similarity	NPD5280	Approved
0.6723	Remote Similarity	NPD6079	Approved
0.6723	Remote Similarity	NPD5694	Approved
0.6721	Remote Similarity	NPD5173	Approved
0.6696	Remote Similarity	NPD3666	Approved
0.6696	Remote Similarity	NPD3133	Approved
0.6696	Remote Similarity	NPD3665	Phase 1
0.6696	Remote Similarity	NPD4197	Approved
0.6695	Remote Similarity	NPD5328	Approved
0.6693	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8449	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6642	Remote Similarity	NPD4522	Approved
0.6639	Remote Similarity	NPD4697	Phase 3
0.662	Remote Similarity	NPD8450	Suspended
0.6617	Remote Similarity	NPD7115	Discovery
0.6615	Remote Similarity	NPD5127	Approved
0.661	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6903	Approved
0.6596	Remote Similarity	NPD7260	Phase 2
0.6583	Remote Similarity	NPD5284	Approved
0.6583	Remote Similarity	NPD5281	Approved
0.6583	Remote Similarity	NPD5693	Phase 1
0.6581	Remote Similarity	NPD6684	Approved
0.6581	Remote Similarity	NPD7146	Approved
0.6581	Remote Similarity	NPD6409	Approved
0.6581	Remote Similarity	NPD7521	Approved
0.6581	Remote Similarity	NPD5330	Approved
0.6581	Remote Similarity	NPD6098	Approved
0.6581	Remote Similarity	NPD7334	Approved
0.6557	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6845	Suspended
0.6544	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6868	Approved
0.6529	Remote Similarity	NPD6399	Phase 3
0.6524	Remote Similarity	NPD7799	Discontinued
0.6522	Remote Similarity	NPD4221	Approved
0.6522	Remote Similarity	NPD4223	Phase 3
0.65	Remote Similarity	NPD5207	Approved
0.6475	Remote Similarity	NPD7748	Approved
0.6466	Remote Similarity	NPD5167	Approved
0.6466	Remote Similarity	NPD4788	Approved
0.6452	Remote Similarity	NPD7902	Approved
0.6423	Remote Similarity	NPD5654	Approved
0.641	Remote Similarity	NPD4786	Approved
0.64	Remote Similarity	NPD7638	Approved
0.6385	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7639	Approved
0.6349	Remote Similarity	NPD7640	Approved
0.6327	Remote Similarity	NPD6334	Approved
0.6327	Remote Similarity	NPD6333	Approved
0.632	Remote Similarity	NPD5959	Approved
0.6319	Remote Similarity	NPD8338	Approved
0.6311	Remote Similarity	NPD7515	Phase 2
0.6303	Remote Similarity	NPD3618	Phase 1
0.6303	Remote Similarity	NPD4689	Approved
0.6303	Remote Similarity	NPD4693	Phase 3

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