NPASS Compound

Structure

NPC476277 OpenBabel07101718332D 29 32 0 0 1 0 0 0 0 0999 V2000 3.2608 3.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9850 -2.3048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6178 -4.3535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0896 -0.8954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3009 1.0594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8669 2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9035 2.3487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9401 -2.4163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -0.9633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5666 0.0469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1084 -1.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7836 -1.3573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1156 0.5790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9401 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -2.9006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6178 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1012 -0.9633 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6178 -2.4163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4184 0.5581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9475 0.2014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4318 -0.6375 0.0000 C 0 0 2 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 -0.0278 1.4178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3414 1.0863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -3.8692 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1862 -1.2450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9563 0.1541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5391 -1.1483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5391 -2.7156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 12 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 14 1 0 0 0 0 9 16 2 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 11 28 1 0 0 0 0 11 29 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 6 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 15 18 2 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 28 1 0 0 0 0 17 22 1 1 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 21 1 1 0 0 0 20 22 1 0 0 0 0 20 24 1 0 0 0 0 21 26 1 1 0 0 0 22 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	400.555
LogP:	2.644
LogD:	2.592
LogS:	-4.103
# Rotatable Bonds:	6
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.732
Synthetic Accessibility Score:	5.4
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.597
MDCK Permeability:	1.7969032342080027e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.891
Plasma Protein Binding (PPB):	80.62088775634766%
Volume Distribution (VD):	1.673
Pgp-substrate:	8.833292961120605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.295
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.235
CYP2D6-inhibitor:	0.827
CYP2D6-substrate:	0.802
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.683

ADMET: Excretion

Clearance (CL):	6.088
Half-life (T1/2):	0.609

ADMET: Toxicity

hERG Blockers:	0.529
Human Hepatotoxicity (H-HT):	0.733
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.281
Rat Oral Acute Toxicity:	0.956
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.421
Carcinogencity:	0.69
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC476277

Natural Product ID:	NPC476277
*Common Name:**	Cinerin C
IUPAC Name:	(1R,5R,6S,7R,8S)-8-hydroxy-1,5-dimethoxy-6-(7-methoxy-1,3-benzodioxol-5-yl)-7-methyl-3-prop-2-enylbicyclo[3.2.1]oct-2-en-4-one
Synonyms:	Cinerin C
Standard InCHIKey:	WEUKJHJYSZGNIC-WYGHCGJFSA-N
Standard InCHI:	InChI=1S/C22H26O7/c1-6-7-13-10-21(26-4)12(2)17(22(27-5,19(13)23)20(21)24)14-8-15(25-3)18-16(9-14)28-11-29-18/h6,8-10,12,17,20,24H,1,7,11H2,2-5H3/t12-,17+,20+,21+,22+/m1/s1
SMILES:	C=CCC1=C[C@@]2([C@H](C)[C@@H](c3cc(c4c(c3)OCO4)OC)[C@](C1=O)([C@H]2O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL561053
PubChem CID:	44232714
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19548690]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO15473	Ocotea heterochroma	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[30188730]
NPO15473	Ocotea heterochroma	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27964	Nectandra amazonum	Species	Lauraceae	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	8
Others	11

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	5
Organism	9
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	28300.0	nM	PMID[479581]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	356000.0	nM	PMID[479581]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1100.0	nM	PMID[479580]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	GI	=	49.4	%	PMID[479580]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	GI	=	49.8	%	PMID[479580]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	GI	=	43.8	%	PMID[479580]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	100.0	%	PMID[479580]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	GI	<	30.0	%	PMID[479580]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	GI	<	30.0	%	PMID[479580]
NPT19	Organism	Escherichia coli	Escherichia coli	GI	<	30.0	%	PMID[479580]
NPT1117	Organism	Salmonella enterica subsp. enterica	Salmonella enterica subsp. enterica	GI	<	30.0	%	PMID[479580]
NPT2	Others	Unspecified		IC50	=	136000.0	nM	PMID[479581]
NPT2	Others	Unspecified		Ratio IC50	=	0.0795	n.a.	PMID[479581]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1090.0	nM	PMID[479581]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	85800.0	nM	PMID[479581]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	999000.0	nM	PMID[479581]
NPT2	Others	Unspecified		IC50	=	1090.0	nM	PMID[479582]

☑ 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 NPC476277 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	389
0.1-0.2	1428
0.2-0.3	3290
0.3-0.4	7450
0.4-0.5	10618
0.5-0.6	6105
0.6-0.7	8596
0.7-0.8	4710
0.8-0.85	85
0.85-0.9	18
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9679	High Similarity	NPC476337
0.9557	High Similarity	NPC476244
0.9551	High Similarity	NPC476340
0.9359	High Similarity	NPC476364
0.9299	High Similarity	NPC476363
0.9231	High Similarity	NPC476335
0.8987	High Similarity	NPC28724
0.891	High Similarity	NPC476338
0.891	High Similarity	NPC476359
0.8797	High Similarity	NPC472567
0.8773	High Similarity	NPC472565
0.8726	High Similarity	NPC476362
0.8688	High Similarity	NPC163002
0.8671	High Similarity	NPC476336
0.8659	High Similarity	NPC475095
0.8596	High Similarity	NPC107739
0.8547	High Similarity	NPC23593
0.8509	High Similarity	NPC475170
0.8481	Intermediate Similarity	NPC15743
0.8448	Intermediate Similarity	NPC236089
0.8439	Intermediate Similarity	NPC263955
0.8408	Intermediate Similarity	NPC51681
0.8395	Intermediate Similarity	NPC177830
0.8395	Intermediate Similarity	NPC12854
0.8391	Intermediate Similarity	NPC29587
0.8354	Intermediate Similarity	NPC327225
0.8344	Intermediate Similarity	NPC62354
0.8324	Intermediate Similarity	NPC71385
0.8324	Intermediate Similarity	NPC230670
0.8323	Intermediate Similarity	NPC25496
0.8303	Intermediate Similarity	NPC25127
0.8294	Intermediate Similarity	NPC475738
0.8293	Intermediate Similarity	NPC56184
0.8293	Intermediate Similarity	NPC151425
0.8284	Intermediate Similarity	NPC206815
0.8278	Intermediate Similarity	NPC112708
0.8274	Intermediate Similarity	NPC474936
0.8266	Intermediate Similarity	NPC470685
0.8263	Intermediate Similarity	NPC220462
0.8261	Intermediate Similarity	NPC472560
0.825	Intermediate Similarity	NPC50696
0.8235	Intermediate Similarity	NPC469518
0.8235	Intermediate Similarity	NPC469475
0.8232	Intermediate Similarity	NPC473711
0.8229	Intermediate Similarity	NPC156635
0.8221	Intermediate Similarity	NPC477698
0.8214	Intermediate Similarity	NPC76211
0.8214	Intermediate Similarity	NPC179914
0.8198	Intermediate Similarity	NPC474948
0.8198	Intermediate Similarity	NPC42230
0.8193	Intermediate Similarity	NPC136757
0.8193	Intermediate Similarity	NPC287504
0.8187	Intermediate Similarity	NPC472564
0.8187	Intermediate Similarity	NPC474966
0.8176	Intermediate Similarity	NPC476011
0.8176	Intermediate Similarity	NPC76687
0.8176	Intermediate Similarity	NPC476334
0.8156	Intermediate Similarity	NPC299855
0.8156	Intermediate Similarity	NPC96194
0.8155	Intermediate Similarity	NPC474990
0.8148	Intermediate Similarity	NPC30890
0.814	Intermediate Similarity	NPC301910
0.814	Intermediate Similarity	NPC113093
0.814	Intermediate Similarity	NPC130730
0.8129	Intermediate Similarity	NPC475865
0.8121	Intermediate Similarity	NPC164082
0.8121	Intermediate Similarity	NPC178048
0.8121	Intermediate Similarity	NPC475379
0.8114	Intermediate Similarity	NPC474568
0.8113	Intermediate Similarity	NPC322021
0.8113	Intermediate Similarity	NPC470855
0.8111	Intermediate Similarity	NPC189704
0.811	Intermediate Similarity	NPC474903
0.8107	Intermediate Similarity	NPC209473
0.8107	Intermediate Similarity	NPC477410
0.8103	Intermediate Similarity	NPC72249
0.8103	Intermediate Similarity	NPC212748
0.8101	Intermediate Similarity	NPC166184
0.8081	Intermediate Similarity	NPC475953
0.8079	Intermediate Similarity	NPC67302
0.8072	Intermediate Similarity	NPC95498
0.8072	Intermediate Similarity	NPC246566
0.8072	Intermediate Similarity	NPC477699
0.807	Intermediate Similarity	NPC125991
0.807	Intermediate Similarity	NPC469512
0.8066	Intermediate Similarity	NPC476067
0.8066	Intermediate Similarity	NPC475121
0.8059	Intermediate Similarity	NPC239818
0.8059	Intermediate Similarity	NPC310399
0.8059	Intermediate Similarity	NPC73422
0.8059	Intermediate Similarity	NPC218471
0.8057	Intermediate Similarity	NPC222665
0.8057	Intermediate Similarity	NPC149502
0.8057	Intermediate Similarity	NPC271755
0.8057	Intermediate Similarity	NPC469506
0.8057	Intermediate Similarity	NPC254071
0.8047	Intermediate Similarity	NPC475663
0.8047	Intermediate Similarity	NPC286919
0.8046	Intermediate Similarity	NPC476771
0.8045	Intermediate Similarity	NPC473883
0.8045	Intermediate Similarity	NPC186746
0.8036	Intermediate Similarity	NPC475484
0.8036	Intermediate Similarity	NPC267242
0.8036	Intermediate Similarity	NPC164152
0.8035	Intermediate Similarity	NPC282551
0.8034	Intermediate Similarity	NPC244903
0.8025	Intermediate Similarity	NPC145769
0.8024	Intermediate Similarity	NPC44730
0.8024	Intermediate Similarity	NPC308555
0.8023	Intermediate Similarity	NPC472582
0.8023	Intermediate Similarity	NPC471286
0.8012	Intermediate Similarity	NPC234152
0.8012	Intermediate Similarity	NPC477700
0.8012	Intermediate Similarity	NPC32079
0.8012	Intermediate Similarity	NPC104956
0.8012	Intermediate Similarity	NPC90336
0.8012	Intermediate Similarity	NPC295009
0.8012	Intermediate Similarity	NPC260640
0.8011	Intermediate Similarity	NPC475360
0.8	Intermediate Similarity	NPC62518
0.8	Intermediate Similarity	NPC215375
0.8	Intermediate Similarity	NPC477883
0.8	Intermediate Similarity	NPC216223
0.8	Intermediate Similarity	NPC278076
0.8	Intermediate Similarity	NPC469384
0.8	Intermediate Similarity	NPC329743
0.8	Intermediate Similarity	NPC145569
0.7989	Intermediate Similarity	NPC283041
0.7989	Intermediate Similarity	NPC471180
0.7989	Intermediate Similarity	NPC149244
0.7989	Intermediate Similarity	NPC6709
0.7989	Intermediate Similarity	NPC48640
0.7989	Intermediate Similarity	NPC42892
0.7989	Intermediate Similarity	NPC170203
0.7988	Intermediate Similarity	NPC153620
0.7988	Intermediate Similarity	NPC24257
0.7988	Intermediate Similarity	NPC475378
0.7988	Intermediate Similarity	NPC30720
0.7988	Intermediate Similarity	NPC189730
0.7977	Intermediate Similarity	NPC474647
0.7977	Intermediate Similarity	NPC180586
0.7976	Intermediate Similarity	NPC60084
0.7976	Intermediate Similarity	NPC478213
0.7975	Intermediate Similarity	NPC474158
0.7975	Intermediate Similarity	NPC476843
0.7975	Intermediate Similarity	NPC476841
0.7975	Intermediate Similarity	NPC327052
0.7966	Intermediate Similarity	NPC108202
0.7965	Intermediate Similarity	NPC41009
0.7965	Intermediate Similarity	NPC302741
0.7955	Intermediate Similarity	NPC476772
0.7955	Intermediate Similarity	NPC475825
0.7955	Intermediate Similarity	NPC245452
0.7955	Intermediate Similarity	NPC471181
0.7955	Intermediate Similarity	NPC223375
0.7955	Intermediate Similarity	NPC121333
0.7955	Intermediate Similarity	NPC235575
0.7953	Intermediate Similarity	NPC472962
0.7953	Intermediate Similarity	NPC285973
0.7953	Intermediate Similarity	NPC472961
0.7953	Intermediate Similarity	NPC474770
0.7953	Intermediate Similarity	NPC269906
0.7953	Intermediate Similarity	NPC225624
0.7952	Intermediate Similarity	NPC147224
0.7944	Intermediate Similarity	NPC473776
0.7944	Intermediate Similarity	NPC473205
0.7943	Intermediate Similarity	NPC21956
0.7943	Intermediate Similarity	NPC152477
0.7941	Intermediate Similarity	NPC223335
0.7941	Intermediate Similarity	NPC167595
0.7941	Intermediate Similarity	NPC40920
0.7941	Intermediate Similarity	NPC473395
0.7939	Intermediate Similarity	NPC304821
0.7939	Intermediate Similarity	NPC308178
0.7935	Intermediate Similarity	NPC475299
0.7933	Intermediate Similarity	NPC108191
0.7933	Intermediate Similarity	NPC93685
0.7931	Intermediate Similarity	NPC255615
0.7931	Intermediate Similarity	NPC173292
0.7931	Intermediate Similarity	NPC67037
0.7931	Intermediate Similarity	NPC254306
0.7931	Intermediate Similarity	NPC20237
0.7931	Intermediate Similarity	NPC119589
0.7929	Intermediate Similarity	NPC284353
0.7929	Intermediate Similarity	NPC254163
0.7929	Intermediate Similarity	NPC38699
0.7929	Intermediate Similarity	NPC478238
0.7927	Intermediate Similarity	NPC296575
0.7927	Intermediate Similarity	NPC224687
0.7927	Intermediate Similarity	NPC212697
0.7919	Intermediate Similarity	NPC124038
0.7919	Intermediate Similarity	NPC476822
0.7917	Intermediate Similarity	NPC245948
0.7917	Intermediate Similarity	NPC104728
0.7917	Intermediate Similarity	NPC153008
0.7917	Intermediate Similarity	NPC35544
0.7917	Intermediate Similarity	NPC473236
0.7917	Intermediate Similarity	NPC148497
0.7914	Intermediate Similarity	NPC475000
0.7914	Intermediate Similarity	NPC27159

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 NPC476277 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	879
0.2-0.3	2018
0.3-0.4	2724
0.4-0.5	1885
0.5-0.6	953
0.6-0.7	298
0.7-0.8	64
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
0.8129	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7199	Phase 2
0.7989	Intermediate Similarity	NPD3818	Discontinued
0.7933	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD37	Approved
0.791	Intermediate Similarity	NPD7685	Pre-registration
0.7904	Intermediate Similarity	NPD7028	Phase 2
0.7882	Intermediate Similarity	NPD3882	Suspended
0.7882	Intermediate Similarity	NPD4967	Phase 2
0.7882	Intermediate Similarity	NPD4965	Approved
0.7882	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD6234	Discontinued
0.7725	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7808	Phase 3
0.7667	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6797	Phase 2
0.7644	Intermediate Similarity	NPD5494	Approved
0.7616	Intermediate Similarity	NPD3817	Phase 2
0.7611	Intermediate Similarity	NPD7251	Discontinued
0.7598	Intermediate Similarity	NPD7074	Phase 3
0.7584	Intermediate Similarity	NPD3751	Discontinued
0.7584	Intermediate Similarity	NPD7228	Approved
0.7545	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD1934	Approved
0.7472	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6166	Phase 2
0.7472	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD3787	Discontinued
0.7457	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7240	Approved
0.7401	Intermediate Similarity	NPD1247	Approved
0.7386	Intermediate Similarity	NPD919	Approved
0.7356	Intermediate Similarity	NPD2801	Approved
0.7337	Intermediate Similarity	NPD6799	Approved
0.7333	Intermediate Similarity	NPD7473	Discontinued
0.733	Intermediate Similarity	NPD7075	Discontinued
0.7322	Intermediate Similarity	NPD6559	Discontinued
0.7321	Intermediate Similarity	NPD6190	Approved
0.7299	Intermediate Similarity	NPD6801	Discontinued
0.7293	Intermediate Similarity	NPD7799	Discontinued
0.7283	Intermediate Similarity	NPD4380	Phase 2
0.7283	Intermediate Similarity	NPD6599	Discontinued
0.7267	Intermediate Similarity	NPD3027	Phase 3
0.7263	Intermediate Similarity	NPD6232	Discontinued
0.7249	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3926	Phase 2
0.7175	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5760	Phase 2
0.7159	Intermediate Similarity	NPD5761	Phase 2
0.7158	Intermediate Similarity	NPD5844	Phase 1
0.7151	Intermediate Similarity	NPD1512	Approved
0.7128	Intermediate Similarity	NPD8434	Phase 2
0.7119	Intermediate Similarity	NPD5402	Approved
0.7111	Intermediate Similarity	NPD8127	Discontinued
0.7093	Intermediate Similarity	NPD2533	Approved
0.7093	Intermediate Similarity	NPD2532	Approved
0.7093	Intermediate Similarity	NPD2534	Approved
0.7093	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD230	Phase 1
0.7083	Intermediate Similarity	NPD6002	Phase 3
0.7083	Intermediate Similarity	NPD5762	Approved
0.7083	Intermediate Similarity	NPD6005	Phase 3
0.7083	Intermediate Similarity	NPD6004	Phase 3
0.7083	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5763	Approved
0.7081	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1653	Approved
0.7062	Intermediate Similarity	NPD7819	Suspended
0.7059	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6764	Approved
0.7043	Intermediate Similarity	NPD6765	Approved
0.7035	Intermediate Similarity	NPD1511	Approved
0.703	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6355	Discontinued
0.6981	Remote Similarity	NPD3705	Approved
0.6979	Remote Similarity	NPD7296	Approved
0.6975	Remote Similarity	NPD5647	Approved
0.6964	Remote Similarity	NPD1510	Phase 2
0.6963	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4628	Phase 3
0.6946	Remote Similarity	NPD6653	Approved
0.6941	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1240	Approved
0.6927	Remote Similarity	NPD5353	Approved
0.6923	Remote Similarity	NPD2796	Approved
0.6914	Remote Similarity	NPD5403	Approved
0.6904	Remote Similarity	NPD6776	Approved
0.6904	Remote Similarity	NPD6781	Approved
0.6904	Remote Similarity	NPD6778	Approved
0.6904	Remote Similarity	NPD6782	Approved
0.6904	Remote Similarity	NPD6780	Approved
0.6904	Remote Similarity	NPD6777	Approved
0.6904	Remote Similarity	NPD6779	Approved
0.6902	Remote Similarity	NPD2403	Approved
0.6901	Remote Similarity	NPD2800	Approved
0.6897	Remote Similarity	NPD5401	Approved
0.6895	Remote Similarity	NPD6784	Approved
0.6895	Remote Similarity	NPD6785	Approved
0.6884	Remote Similarity	NPD7435	Discontinued
0.6864	Remote Similarity	NPD651	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4110	Phase 3
0.686	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5242	Approved
0.6845	Remote Similarity	NPD1607	Approved
0.6842	Remote Similarity	NPD1549	Phase 2
0.6833	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD9494	Approved
0.6826	Remote Similarity	NPD3620	Phase 2
0.6826	Remote Similarity	NPD943	Approved
0.6826	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD920	Approved
0.6813	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7680	Approved
0.6792	Remote Similarity	NPD1357	Approved
0.679	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7266	Discontinued
0.6782	Remote Similarity	NPD7236	Approved
0.6778	Remote Similarity	NPD1465	Phase 2
0.6761	Remote Similarity	NPD6273	Approved
0.676	Remote Similarity	NPD7411	Suspended
0.6744	Remote Similarity	NPD2424	Discontinued
0.6743	Remote Similarity	NPD4357	Discontinued
0.6742	Remote Similarity	NPD7458	Discontinued
0.6726	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1613	Approved
0.6725	Remote Similarity	NPD2935	Discontinued
0.6716	Remote Similarity	NPD7696	Phase 3
0.6716	Remote Similarity	NPD7697	Approved
0.6716	Remote Similarity	NPD7698	Approved
0.6705	Remote Similarity	NPD6674	Discontinued
0.6705	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7229	Phase 3
0.6702	Remote Similarity	NPD8313	Approved
0.6702	Remote Similarity	NPD8312	Approved
0.6686	Remote Similarity	NPD5735	Approved
0.6686	Remote Similarity	NPD447	Suspended
0.6684	Remote Similarity	NPD8150	Discontinued
0.6683	Remote Similarity	NPD7874	Approved
0.6683	Remote Similarity	NPD7871	Phase 2
0.6683	Remote Similarity	NPD7870	Phase 2
0.6683	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD8407	Phase 2
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5536	Phase 2
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD7701	Phase 2
0.665	Remote Similarity	NPD6535	Approved
0.665	Remote Similarity	NPD7801	Approved
0.665	Remote Similarity	NPD6534	Approved
0.6649	Remote Similarity	NPD6959	Discontinued
0.6647	Remote Similarity	NPD6651	Approved
0.6634	Remote Similarity	NPD8151	Discontinued
0.6634	Remote Similarity	NPD7497	Discontinued
0.6628	Remote Similarity	NPD6100	Approved
0.6628	Remote Similarity	NPD6099	Approved
0.662	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD5711	Approved
0.6613	Remote Similarity	NPD5710	Approved
0.661	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD1243	Approved
0.6607	Remote Similarity	NPD6798	Discontinued
0.6601	Remote Similarity	NPD8320	Phase 1
0.6601	Remote Similarity	NPD8319	Approved
0.6597	Remote Similarity	NPD8368	Discontinued
0.6593	Remote Similarity	NPD8455	Phase 2
0.6592	Remote Similarity	NPD7239	Suspended
0.6591	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5005	Approved
0.6584	Remote Similarity	NPD5006	Approved
0.6583	Remote Similarity	NPD2975	Approved
0.6583	Remote Similarity	NPD2973	Approved
0.6583	Remote Similarity	NPD2974	Approved
0.6576	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6385	Approved
0.6575	Remote Similarity	NPD5090	Approved
0.6575	Remote Similarity	NPD5089	Approved
0.6575	Remote Similarity	NPD6386	Approved
0.6571	Remote Similarity	NPD8166	Discontinued
0.6571	Remote Similarity	NPD3750	Approved
0.657	Remote Similarity	NPD2799	Discontinued
0.6567	Remote Similarity	NPD4580	Approved
0.6566	Remote Similarity	NPD2798	Approved
0.6564	Remote Similarity	NPD6842	Approved
0.6564	Remote Similarity	NPD6843	Phase 3
0.6564	Remote Similarity	NPD6841	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