NPASS Compound

Structure

CID227132 OpenBabel06191716022D 33 36 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2942 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 29 1 1 0 0 0 21 30 1 0 0 0 0 22 31 1 6 0 0 0 23 27 1 0 0 0 0 23 29 1 1 0 0 0 24 28 1 0 0 0 0 24 30 1 1 0 0 0 25 27 1 0 0 0 0 25 32 2 0 0 0 0 26 28 1 0 0 0 0 26 33 2 0 0 0 0 29 7 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	509.035
LogP:	4.52
LogD:	4.108
LogS:	-4.557
# Rotatable Bonds:	3
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.475
Synthetic Accessibility Score:	4.799
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.26
MDCK Permeability:	1.2155039257777389e-05
Pgp-inhibitor:	0.721
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.86
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	82.6470718383789%
Volume Distribution (VD):	1.088
Pgp-substrate:	3.211616277694702%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.637
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.944
CYP2C9-inhibitor:	0.416
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.613
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	7.289
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.321
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.648
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.053
Carcinogencity:	0.109
Eye Corrosion:	0.004
Eye Irritation:	0.316
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC227132

Natural Product ID:	NPC227132
*Common Name:**	Lamesticumin D
IUPAC Name:	(4aS,7R,8aR)-5-[2-[(1S,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-6-oxo-1,3,4,4a,7,8-hexahydronaphthalen-1-yl]ethyl]-7-hydroxy-1,1,4a,6-tetramethyl-4,7,8,8a-tetrahydro-3H-naphthalen-2-one
Synonyms:	Lamesticumin D
Standard InCHIKey:	MGVFDWIGIYHFIO-CKQYGLACSA-N
Standard InCHI:	InChI=1S/C30H46O3/c1-18-9-12-23-27(3,4)25(32)13-15-29(23,7)20(18)10-11-21-19(2)22(31)17-24-28(5,6)26(33)14-16-30(21,24)8/h20,22-24,31H,1,9-17H2,2-8H3/t20-,22+,23-,24-,29+,30+/m0/s1
SMILES:	C=C1CC[C@H]2C(C)(C)C(=O)CC[C@]2(C)[C@H]1CCC1=C(C)[C@@H](C[C@H]2C(C)(C)C(=O)CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782132
PubChem CID:	53355686
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	exocarp	n.a.	DOI[10.1021/jo00172a004]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444710]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[19299148]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Mengla County, Yunnan Province, China	2005-AUG	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21401117]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[30335380]
NPO20633	Lansium domesticum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	11

Activity Type	# Activity
Organism	11

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[473864]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	>	50.0	ug.mL-1	PMID[473864]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	50.0	ug.mL-1	PMID[473864]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	6.25	ug.mL-1	PMID[473864]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	3.12	ug.mL-1	PMID[473864]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[473864]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[473864]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[473864]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	50.0	ug.mL-1	PMID[473864]
NPT2227	Organism	Alcaligenes faecalis	Alcaligenes faecalis	MIC	>	50.0	ug.mL-1	PMID[473864]

☑ 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 NPC227132 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	176
0.1-0.2	1227
0.2-0.3	5148
0.3-0.4	14361
0.4-0.5	9649
0.5-0.6	6167
0.6-0.7	4437
0.7-0.8	1455
0.8-0.85	69
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9146	High Similarity	NPC274724
0.881	High Similarity	NPC470955
0.881	High Similarity	NPC322159
0.8721	High Similarity	NPC69627
0.8721	High Similarity	NPC472973
0.8721	High Similarity	NPC281524
0.869	High Similarity	NPC476426
0.869	High Similarity	NPC471224
0.869	High Similarity	NPC133954
0.8659	High Similarity	NPC3915
0.8588	High Similarity	NPC158393
0.8588	High Similarity	NPC213412
0.8588	High Similarity	NPC74363
0.8588	High Similarity	NPC475862
0.8571	High Similarity	NPC473157
0.8571	High Similarity	NPC476412
0.8571	High Similarity	NPC180834
0.8554	High Similarity	NPC310989
0.8523	High Similarity	NPC63748
0.8523	High Similarity	NPC472978
0.8488	Intermediate Similarity	NPC73064
0.8488	Intermediate Similarity	NPC4643
0.8471	Intermediate Similarity	NPC474083
0.8452	Intermediate Similarity	NPC105173
0.8427	Intermediate Similarity	NPC69454
0.8427	Intermediate Similarity	NPC472930
0.8409	Intermediate Similarity	NPC48010
0.8395	Intermediate Similarity	NPC74995
0.8391	Intermediate Similarity	NPC474925
0.8391	Intermediate Similarity	NPC472802
0.8372	Intermediate Similarity	NPC472985
0.8372	Intermediate Similarity	NPC477579
0.8372	Intermediate Similarity	NPC95594
0.8372	Intermediate Similarity	NPC469994
0.8372	Intermediate Similarity	NPC235341
0.8372	Intermediate Similarity	NPC472986
0.8372	Intermediate Similarity	NPC82979
0.8333	Intermediate Similarity	NPC472977
0.8333	Intermediate Similarity	NPC474529
0.8333	Intermediate Similarity	NPC48362
0.8333	Intermediate Similarity	NPC471207
0.8333	Intermediate Similarity	NPC472976
0.8315	Intermediate Similarity	NPC472975
0.8313	Intermediate Similarity	NPC148685
0.8313	Intermediate Similarity	NPC104120
0.8313	Intermediate Similarity	NPC2482
0.8313	Intermediate Similarity	NPC306095
0.8313	Intermediate Similarity	NPC157895
0.8295	Intermediate Similarity	NPC2983
0.8295	Intermediate Similarity	NPC469319
0.8295	Intermediate Similarity	NPC229871
0.8295	Intermediate Similarity	NPC473999
0.8295	Intermediate Similarity	NPC309603
0.8293	Intermediate Similarity	NPC297996
0.8276	Intermediate Similarity	NPC242468
0.8276	Intermediate Similarity	NPC51700
0.8276	Intermediate Similarity	NPC71507
0.8276	Intermediate Similarity	NPC307426
0.8276	Intermediate Similarity	NPC102683
0.8276	Intermediate Similarity	NPC293564
0.8276	Intermediate Similarity	NPC171203
0.8276	Intermediate Similarity	NPC130577
0.8276	Intermediate Similarity	NPC68160
0.8276	Intermediate Similarity	NPC18064
0.8276	Intermediate Similarity	NPC98442
0.8276	Intermediate Similarity	NPC142415
0.8276	Intermediate Similarity	NPC88716
0.8261	Intermediate Similarity	NPC189880
0.8256	Intermediate Similarity	NPC292553
0.8242	Intermediate Similarity	NPC318282
0.8242	Intermediate Similarity	NPC174948
0.8242	Intermediate Similarity	NPC469995
0.8242	Intermediate Similarity	NPC259286
0.8242	Intermediate Similarity	NPC173875
0.8242	Intermediate Similarity	NPC139570
0.8235	Intermediate Similarity	NPC472498
0.8222	Intermediate Similarity	NPC477520
0.8214	Intermediate Similarity	NPC103754
0.8214	Intermediate Similarity	NPC474484
0.8211	Intermediate Similarity	NPC90177
0.8202	Intermediate Similarity	NPC198818
0.8202	Intermediate Similarity	NPC85173
0.8202	Intermediate Similarity	NPC193750
0.8202	Intermediate Similarity	NPC291028
0.8193	Intermediate Similarity	NPC308038
0.8193	Intermediate Similarity	NPC152061
0.8193	Intermediate Similarity	NPC281138
0.8182	Intermediate Similarity	NPC52169
0.8182	Intermediate Similarity	NPC143767
0.8182	Intermediate Similarity	NPC206060
0.8182	Intermediate Similarity	NPC181225
0.8182	Intermediate Similarity	NPC328539
0.8182	Intermediate Similarity	NPC40552
0.8182	Intermediate Similarity	NPC131470
0.8182	Intermediate Similarity	NPC473242
0.8182	Intermediate Similarity	NPC246708
0.8182	Intermediate Similarity	NPC470629
0.8182	Intermediate Similarity	NPC474512
0.8182	Intermediate Similarity	NPC290690
0.8182	Intermediate Similarity	NPC53911
0.8182	Intermediate Similarity	NPC182797
0.8182	Intermediate Similarity	NPC17733
0.8171	Intermediate Similarity	NPC325946
0.8161	Intermediate Similarity	NPC472974
0.8161	Intermediate Similarity	NPC472738
0.8161	Intermediate Similarity	NPC72638
0.8152	Intermediate Similarity	NPC5532
0.8152	Intermediate Similarity	NPC61369
0.8152	Intermediate Similarity	NPC469545
0.8152	Intermediate Similarity	NPC249954
0.8152	Intermediate Similarity	NPC328371
0.814	Intermediate Similarity	NPC221758
0.814	Intermediate Similarity	NPC214043
0.814	Intermediate Similarity	NPC59453
0.814	Intermediate Similarity	NPC82902
0.814	Intermediate Similarity	NPC171789
0.814	Intermediate Similarity	NPC85774
0.8132	Intermediate Similarity	NPC474882
0.8132	Intermediate Similarity	NPC91010
0.8132	Intermediate Similarity	NPC473162
0.8125	Intermediate Similarity	NPC474281
0.8118	Intermediate Similarity	NPC151519
0.8118	Intermediate Similarity	NPC163236
0.8118	Intermediate Similarity	NPC477858
0.8118	Intermediate Similarity	NPC212083
0.8118	Intermediate Similarity	NPC145143
0.8111	Intermediate Similarity	NPC473998
0.8111	Intermediate Similarity	NPC105189
0.8111	Intermediate Similarity	NPC233116
0.8111	Intermediate Similarity	NPC65120
0.8111	Intermediate Similarity	NPC158030
0.8111	Intermediate Similarity	NPC145067
0.8111	Intermediate Similarity	NPC38754
0.8111	Intermediate Similarity	NPC475806
0.8111	Intermediate Similarity	NPC471588
0.8111	Intermediate Similarity	NPC4036
0.8111	Intermediate Similarity	NPC6255
0.8111	Intermediate Similarity	NPC474525
0.8111	Intermediate Similarity	NPC272746
0.8111	Intermediate Similarity	NPC233455
0.8111	Intermediate Similarity	NPC107690
0.8095	Intermediate Similarity	NPC295131
0.8095	Intermediate Similarity	NPC472478
0.8095	Intermediate Similarity	NPC172013
0.809	Intermediate Similarity	NPC184663
0.809	Intermediate Similarity	NPC474686
0.809	Intermediate Similarity	NPC470588
0.809	Intermediate Similarity	NPC472970
0.809	Intermediate Similarity	NPC290972
0.809	Intermediate Similarity	NPC95246
0.809	Intermediate Similarity	NPC61543
0.809	Intermediate Similarity	NPC234346
0.809	Intermediate Similarity	NPC472971
0.809	Intermediate Similarity	NPC293048
0.809	Intermediate Similarity	NPC270768
0.809	Intermediate Similarity	NPC64872
0.809	Intermediate Similarity	NPC161751
0.809	Intermediate Similarity	NPC263393
0.809	Intermediate Similarity	NPC198664
0.809	Intermediate Similarity	NPC130520
0.809	Intermediate Similarity	NPC275740
0.809	Intermediate Similarity	NPC25906
0.809	Intermediate Similarity	NPC59263
0.809	Intermediate Similarity	NPC225585
0.809	Intermediate Similarity	NPC86319
0.809	Intermediate Similarity	NPC127689
0.809	Intermediate Similarity	NPC143232
0.809	Intermediate Similarity	NPC472983
0.809	Intermediate Similarity	NPC121798
0.809	Intermediate Similarity	NPC274330
0.809	Intermediate Similarity	NPC474972
0.8072	Intermediate Similarity	NPC62336
0.8072	Intermediate Similarity	NPC475994
0.8072	Intermediate Similarity	NPC239098
0.8068	Intermediate Similarity	NPC317590
0.8068	Intermediate Similarity	NPC298904
0.8068	Intermediate Similarity	NPC472497
0.8068	Intermediate Similarity	NPC158141
0.8068	Intermediate Similarity	NPC472495
0.8068	Intermediate Similarity	NPC173089
0.8068	Intermediate Similarity	NPC57469
0.8068	Intermediate Similarity	NPC475740
0.8068	Intermediate Similarity	NPC93778
0.8065	Intermediate Similarity	NPC190554
0.8049	Intermediate Similarity	NPC89294
0.8049	Intermediate Similarity	NPC263582
0.8046	Intermediate Similarity	NPC470574
0.8046	Intermediate Similarity	NPC469948
0.8046	Intermediate Similarity	NPC474218
0.8043	Intermediate Similarity	NPC272617
0.8043	Intermediate Similarity	NPC271195
0.8043	Intermediate Similarity	NPC472932
0.8043	Intermediate Similarity	NPC266899
0.8043	Intermediate Similarity	NPC473240
0.8043	Intermediate Similarity	NPC290481
0.8023	Intermediate Similarity	NPC307258
0.8023	Intermediate Similarity	NPC475726
0.8023	Intermediate Similarity	NPC215893
0.8023	Intermediate Similarity	NPC64600
0.8023	Intermediate Similarity	NPC476082

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 NPC227132 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1611
0.2-0.3	3952
0.3-0.4	2388
0.4-0.5	595
0.5-0.6	188
0.6-0.7	216
0.7-0.8	35
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
0.8295	Intermediate Similarity	NPD5328	Approved
0.814	Intermediate Similarity	NPD4786	Approved
0.8118	Intermediate Similarity	NPD3667	Approved
0.8111	Intermediate Similarity	NPD6079	Approved
0.8111	Intermediate Similarity	NPD7515	Phase 2
0.7955	Intermediate Similarity	NPD3618	Phase 1
0.7931	Intermediate Similarity	NPD3666	Approved
0.7931	Intermediate Similarity	NPD3133	Approved
0.7931	Intermediate Similarity	NPD3665	Phase 1
0.7742	Intermediate Similarity	NPD7748	Approved
0.764	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5221	Approved
0.7579	Intermediate Similarity	NPD5222	Approved
0.7579	Intermediate Similarity	NPD4697	Phase 3
0.7579	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7645	Phase 2
0.7556	Intermediate Similarity	NPD4623	Approved
0.7556	Intermediate Similarity	NPD4519	Discontinued
0.7551	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.7447	Intermediate Similarity	NPD4202	Approved
0.7416	Intermediate Similarity	NPD4788	Approved
0.74	Intermediate Similarity	NPD5141	Approved
0.7391	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5279	Phase 3
0.7347	Intermediate Similarity	NPD5286	Approved
0.7347	Intermediate Similarity	NPD4700	Approved
0.7347	Intermediate Similarity	NPD4696	Approved
0.7347	Intermediate Similarity	NPD5285	Approved
0.7333	Intermediate Similarity	NPD3668	Phase 3
0.7312	Intermediate Similarity	NPD4753	Phase 2
0.7303	Intermediate Similarity	NPD4221	Approved
0.7303	Intermediate Similarity	NPD4223	Phase 3
0.7273	Intermediate Similarity	NPD4695	Discontinued
0.7273	Intermediate Similarity	NPD5223	Approved
0.7263	Intermediate Similarity	NPD6399	Phase 3
0.7253	Intermediate Similarity	NPD5329	Approved
0.7241	Intermediate Similarity	NPD3617	Approved
0.72	Intermediate Similarity	NPD5225	Approved
0.72	Intermediate Similarity	NPD4633	Approved
0.72	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD5224	Approved
0.7188	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7900	Approved
0.7174	Intermediate Similarity	NPD5330	Approved
0.7174	Intermediate Similarity	NPD6409	Approved
0.7174	Intermediate Similarity	NPD6684	Approved
0.7174	Intermediate Similarity	NPD7146	Approved
0.7174	Intermediate Similarity	NPD7521	Approved
0.7174	Intermediate Similarity	NPD7334	Approved
0.7172	Intermediate Similarity	NPD7639	Approved
0.7172	Intermediate Similarity	NPD7640	Approved
0.7157	Intermediate Similarity	NPD7128	Approved
0.7157	Intermediate Similarity	NPD6675	Approved
0.7157	Intermediate Similarity	NPD5739	Approved
0.7157	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD4197	Approved
0.7129	Intermediate Similarity	NPD4754	Approved
0.7129	Intermediate Similarity	NPD5175	Approved
0.7129	Intermediate Similarity	NPD5174	Approved
0.7128	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3573	Approved
0.7093	Intermediate Similarity	NPD7339	Approved
0.7093	Intermediate Similarity	NPD6942	Approved
0.7093	Intermediate Similarity	NPD3703	Phase 2
0.7079	Intermediate Similarity	NPD7525	Registered
0.7071	Intermediate Similarity	NPD7638	Approved
0.7045	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4245	Approved
0.7024	Intermediate Similarity	NPD4244	Approved
0.7021	Intermediate Similarity	NPD6903	Approved
0.7019	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD6881	Approved
0.7019	Intermediate Similarity	NPD7320	Approved
0.7011	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4768	Approved
0.699	Remote Similarity	NPD4767	Approved
0.6989	Remote Similarity	NPD5205	Approved
0.6989	Remote Similarity	NPD4693	Phase 3
0.6989	Remote Similarity	NPD4689	Approved
0.6989	Remote Similarity	NPD4138	Approved
0.6989	Remote Similarity	NPD4690	Approved
0.6989	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4688	Approved
0.6979	Remote Similarity	NPD8035	Phase 2
0.6979	Remote Similarity	NPD8034	Phase 2
0.6979	Remote Similarity	NPD6411	Approved
0.697	Remote Similarity	NPD6084	Phase 2
0.697	Remote Similarity	NPD6083	Phase 2
0.6952	Remote Similarity	NPD6372	Approved
0.6952	Remote Similarity	NPD6373	Approved
0.6951	Remote Similarity	NPD7331	Phase 2
0.6941	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4629	Approved
0.6939	Remote Similarity	NPD5210	Approved
0.6923	Remote Similarity	NPD5701	Approved
0.6923	Remote Similarity	NPD5697	Approved
0.6907	Remote Similarity	NPD5779	Approved
0.6907	Remote Similarity	NPD5778	Approved
0.6905	Remote Similarity	NPD4137	Phase 3
0.6905	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3698	Phase 2
0.6897	Remote Similarity	NPD8264	Approved
0.6887	Remote Similarity	NPD7102	Approved
0.6887	Remote Similarity	NPD7290	Approved
0.6887	Remote Similarity	NPD6883	Approved
0.6869	Remote Similarity	NPD7614	Phase 1
0.6857	Remote Similarity	NPD4730	Approved
0.6857	Remote Similarity	NPD5128	Approved
0.6857	Remote Similarity	NPD6011	Approved
0.6857	Remote Similarity	NPD5168	Approved
0.6857	Remote Similarity	NPD4729	Approved
0.6842	Remote Similarity	NPD5737	Approved
0.6842	Remote Similarity	NPD6672	Approved
0.6829	Remote Similarity	NPD7341	Phase 2
0.6824	Remote Similarity	NPD4691	Approved
0.6824	Remote Similarity	NPD4747	Approved
0.6824	Remote Similarity	NPD4789	Approved
0.6822	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD7115	Discovery
0.6813	Remote Similarity	NPD4139	Approved
0.6813	Remote Similarity	NPD4692	Approved
0.6809	Remote Similarity	NPD5690	Phase 2
0.6809	Remote Similarity	NPD4694	Approved
0.6809	Remote Similarity	NPD5280	Approved
0.6792	Remote Similarity	NPD6012	Approved
0.6792	Remote Similarity	NPD6014	Approved
0.6792	Remote Similarity	NPD6013	Approved
0.6786	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6101	Approved
0.6762	Remote Similarity	NPD6412	Phase 2
0.6759	Remote Similarity	NPD6882	Approved
0.6759	Remote Similarity	NPD8297	Approved
0.6737	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5249	Phase 3
0.6729	Remote Similarity	NPD5251	Approved
0.6729	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5247	Approved
0.6729	Remote Similarity	NPD5250	Approved
0.6729	Remote Similarity	NPD5135	Approved
0.6729	Remote Similarity	NPD5169	Approved
0.6729	Remote Similarity	NPD5248	Approved
0.6729	Remote Similarity	NPD4634	Approved
0.6702	Remote Similarity	NPD1696	Phase 3
0.6699	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5216	Approved
0.6667	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD5217	Approved
0.6632	Remote Similarity	NPD6098	Approved
0.6632	Remote Similarity	NPD5786	Approved
0.6629	Remote Similarity	NPD6117	Approved
0.6627	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5695	Phase 3
0.6593	Remote Similarity	NPD6929	Approved
0.6593	Remote Similarity	NPD4195	Approved
0.6591	Remote Similarity	NPD6926	Approved
0.6591	Remote Similarity	NPD6924	Approved
0.6591	Remote Similarity	NPD4058	Approved
0.6591	Remote Similarity	NPD5733	Approved
0.6591	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6868	Approved
0.6569	Remote Similarity	NPD5696	Approved
0.6559	Remote Similarity	NPD4270	Approved
0.6559	Remote Similarity	NPD4269	Approved
0.6559	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD5776	Phase 2
0.6556	Remote Similarity	NPD6925	Approved
0.6556	Remote Similarity	NPD6116	Phase 1
0.6552	Remote Similarity	NPD4243	Approved
0.6545	Remote Similarity	NPD4632	Approved
0.6535	Remote Similarity	NPD7732	Phase 3
0.6526	Remote Similarity	NPD1694	Approved
0.6522	Remote Similarity	NPD7514	Phase 3
0.6522	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5368	Approved
0.6522	Remote Similarity	NPD7332	Phase 2
0.6522	Remote Similarity	NPD6931	Approved
0.6522	Remote Similarity	NPD6930	Phase 2
0.6512	Remote Similarity	NPD6922	Approved
0.6512	Remote Similarity	NPD6923	Approved
0.6489	Remote Similarity	NPD5362	Discontinued
0.6486	Remote Similarity	NPD5167	Approved
0.6484	Remote Similarity	NPD7145	Approved
0.6484	Remote Similarity	NPD6697	Approved
0.6484	Remote Similarity	NPD6115	Approved
0.6484	Remote Similarity	NPD6114	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