NPASS Compound

Structure

CID80144 OpenBabel06191715422D 30 33 0 0 1 0 0 0 0 0999 V2000 3.4159 3.3156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7020 1.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7059 -0.9404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8626 2.2773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7247 1.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0850 2.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7885 0.7791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5126 0.0407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7058 1.6472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9224 1.2791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0449 2.8529 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6053 0.4611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1928 0.7738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0299 1.9998 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1793 0.6100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5805 -0.1991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8734 0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2087 3.8394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7019 2.0257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0449 2.9997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7618 1.9739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2497 -0.9422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 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 5.5860 -0.3036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 8 2 0 0 0 0 3 9 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 22 1 0 0 0 0 7 10 1 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 10 5 1 1 0 0 0 10 15 1 0 0 0 0 11 4 1 1 0 0 0 11 19 1 0 0 0 0 12 23 1 6 0 0 0 13 28 1 1 0 0 0 14 6 1 6 0 0 0 14 16 1 0 0 0 0 14 29 1 0 0 0 0 15 9 1 1 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 1 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 21 1 0 0 0 0 18 26 1 1 0 0 0 19 30 1 6 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 28 1 6 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.17
Volume:	406.113
LogP:	-0.167
LogD:	0.136
LogS:	-1.858
# Rotatable Bonds:	3
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.214
Synthetic Accessibility Score:	5.222
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.092
MDCK Permeability:	8.553637599106878e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.354
Human Intestinal Absorption (HIA):	0.894
20% Bioavailability (F20%):	0.567
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	57.952396392822266%
Volume Distribution (VD):	0.603
Pgp-substrate:	43.12639236450195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.212
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.008
CYP3A4-substrate:	0.12

ADMET: Excretion

Clearance (CL):	1.717
Half-life (T1/2):	0.479

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.823
Drug-inuced Liver Injury (DILI):	0.7
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.72
Maximum Recommended Daily Dose:	0.976
Skin Sensitization:	0.208
Carcinogencity:	0.278
Eye Corrosion:	0.009
Eye Irritation:	0.107
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC80144

Natural Product ID:	NPC80144
*Common Name:**	Macrocliniside A
IUPAC Name:	(3aS,5R,6aR,8S,9aR,9bS)-5-hydroxy-3,6,9-trimethylidene-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	ARJUJAMZTUUZNZ-NJQUUYHGSA-N
Standard InCHI:	InChI=1S/C21H28O9/c1-7-10-5-13(28-21-18(26)17(25)16(24)14(6-22)29-21)9(3)15(10)19-11(4-12(7)23)8(2)20(27)30-19/h10-19,21-26H,1-6H2/t10-,11-,12+,13-,14+,15-,16+,17-,18+,19-,21+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2C[C@@H]3[C@H](C2=C)[C@H]2OC(=O)C(=C)[C@@H]2C[C@H](C3=C)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622760
PubChem CID:	10455028
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*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
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90113-8]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14987049]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17567070]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	seed	n.a.	PMID[21280632]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21648406]
NPO32813	ixeris dentata	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[26341134]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13	Chamaecrista mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13	Chamaecrista mimosoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO372	Kallstroemia tribuloides	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4787	Capuronianthus mahafalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO782	Viola tricolor	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10756	Callitris drummondii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1854	Cardiospermum hirsutum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4346	Leonurus cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5855	Scutellaria repens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4151	Rhamnus wightii	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8975	Aconitum nemorum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9352	Senecio peltiferus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2434	Lipotriche scandens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2438	Euryale ferox	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8002	Solanum olgae	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
Others	4

Activity Type	# Activity
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	19.7	uM	PMID[485041]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	18.7	uM	PMID[485041]
NPT27	Others	Unspecified		Activity	=	109.8	%	PMID[485041]
NPT27	Others	Unspecified		Activity	=	109.6	%	PMID[485041]

☑ 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 NPC80144 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	255
0.1-0.2	1695
0.2-0.3	6121
0.3-0.4	12390
0.4-0.5	10602
0.5-0.6	7355
0.6-0.7	3784
0.7-0.8	445
0.8-0.85	38
0.85-0.9	3
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC67296
0.9681	High Similarity	NPC49833
0.9681	High Similarity	NPC249171
0.9368	High Similarity	NPC236580
0.9368	High Similarity	NPC304445
0.9286	High Similarity	NPC473148
0.9263	High Similarity	NPC474297
0.8958	High Similarity	NPC167893
0.8776	High Similarity	NPC58267
0.8776	High Similarity	NPC261372
0.8776	High Similarity	NPC263674
0.8725	High Similarity	NPC170432
0.8713	High Similarity	NPC475928
0.8673	High Similarity	NPC161293
0.8641	High Similarity	NPC148270
0.8641	High Similarity	NPC80338
0.8641	High Similarity	NPC197813
0.8614	High Similarity	NPC474730
0.8614	High Similarity	NPC177013
0.8614	High Similarity	NPC4899
0.8614	High Similarity	NPC35185
0.8586	High Similarity	NPC471150
0.8544	High Similarity	NPC127235
0.8529	High Similarity	NPC37240
0.8526	High Similarity	NPC207114
0.8526	High Similarity	NPC217983
0.8515	High Similarity	NPC287539
0.8515	High Similarity	NPC3488
0.8511	High Similarity	NPC187661
0.8438	Intermediate Similarity	NPC38392
0.8431	Intermediate Similarity	NPC106668
0.84	Intermediate Similarity	NPC474313
0.8396	Intermediate Similarity	NPC193741
0.8381	Intermediate Similarity	NPC110701
0.8351	Intermediate Similarity	NPC19087
0.835	Intermediate Similarity	NPC27687
0.8317	Intermediate Similarity	NPC472015
0.8298	Intermediate Similarity	NPC224386
0.8298	Intermediate Similarity	NPC194859
0.8265	Intermediate Similarity	NPC184063
0.8241	Intermediate Similarity	NPC475924
0.8241	Intermediate Similarity	NPC475851
0.8235	Intermediate Similarity	NPC186861
0.8235	Intermediate Similarity	NPC471381
0.8235	Intermediate Similarity	NPC473146
0.82	Intermediate Similarity	NPC476053
0.82	Intermediate Similarity	NPC472873
0.8163	Intermediate Similarity	NPC54065
0.8163	Intermediate Similarity	NPC297474
0.8137	Intermediate Similarity	NPC37866
0.8119	Intermediate Similarity	NPC91771
0.8119	Intermediate Similarity	NPC476009
0.8119	Intermediate Similarity	NPC142529
0.8081	Intermediate Similarity	NPC35959
0.8081	Intermediate Similarity	NPC171360
0.8081	Intermediate Similarity	NPC475925
0.8081	Intermediate Similarity	NPC29821
0.8081	Intermediate Similarity	NPC133888
0.8081	Intermediate Similarity	NPC57304
0.8081	Intermediate Similarity	NPC293001
0.8081	Intermediate Similarity	NPC63193
0.8061	Intermediate Similarity	NPC155935
0.8061	Intermediate Similarity	NPC92974
0.8061	Intermediate Similarity	NPC215556
0.8041	Intermediate Similarity	NPC190753
0.8041	Intermediate Similarity	NPC118601
0.8041	Intermediate Similarity	NPC186148
0.8039	Intermediate Similarity	NPC472290
0.802	Intermediate Similarity	NPC163228
0.8019	Intermediate Similarity	NPC54737
0.8	Intermediate Similarity	NPC128246
0.8	Intermediate Similarity	NPC475788
0.798	Intermediate Similarity	NPC206614
0.798	Intermediate Similarity	NPC474323
0.798	Intermediate Similarity	NPC216284
0.798	Intermediate Similarity	NPC35809
0.7963	Intermediate Similarity	NPC139838
0.7963	Intermediate Similarity	NPC59489
0.7959	Intermediate Similarity	NPC177629
0.7959	Intermediate Similarity	NPC178875
0.7959	Intermediate Similarity	NPC58219
0.7959	Intermediate Similarity	NPC79549
0.7941	Intermediate Similarity	NPC306041
0.7938	Intermediate Similarity	NPC309757
0.7938	Intermediate Similarity	NPC304558
0.7938	Intermediate Similarity	NPC236692
0.7905	Intermediate Similarity	NPC250545
0.79	Intermediate Similarity	NPC235051
0.7895	Intermediate Similarity	NPC246076
0.787	Intermediate Similarity	NPC475960
0.7864	Intermediate Similarity	NPC311904
0.7864	Intermediate Similarity	NPC181151
0.7857	Intermediate Similarity	NPC277583
0.785	Intermediate Similarity	NPC223450
0.785	Intermediate Similarity	NPC243998
0.7843	Intermediate Similarity	NPC475900
0.7843	Intermediate Similarity	NPC36954
0.7826	Intermediate Similarity	NPC470829
0.7826	Intermediate Similarity	NPC473228
0.7822	Intermediate Similarity	NPC200237
0.7822	Intermediate Similarity	NPC258216
0.7822	Intermediate Similarity	NPC475912
0.781	Intermediate Similarity	NPC150923
0.781	Intermediate Similarity	NPC171759
0.7789	Intermediate Similarity	NPC126248
0.7788	Intermediate Similarity	NPC45125
0.7778	Intermediate Similarity	NPC470009
0.7778	Intermediate Similarity	NPC471149
0.7767	Intermediate Similarity	NPC24956
0.7767	Intermediate Similarity	NPC54731
0.7767	Intermediate Similarity	NPC18019
0.7755	Intermediate Similarity	NPC476015
0.7755	Intermediate Similarity	NPC474949
0.7755	Intermediate Similarity	NPC56593
0.7755	Intermediate Similarity	NPC475019
0.7755	Intermediate Similarity	NPC474762
0.7755	Intermediate Similarity	NPC470242
0.7745	Intermediate Similarity	NPC198853
0.7745	Intermediate Similarity	NPC71589
0.7745	Intermediate Similarity	NPC63897
0.7745	Intermediate Similarity	NPC190294
0.7745	Intermediate Similarity	NPC473331
0.7736	Intermediate Similarity	NPC310804
0.7736	Intermediate Similarity	NPC304163
0.7736	Intermediate Similarity	NPC86077
0.7736	Intermediate Similarity	NPC261117
0.7732	Intermediate Similarity	NPC3464
0.7732	Intermediate Similarity	NPC151176
0.7732	Intermediate Similarity	NPC475963
0.7732	Intermediate Similarity	NPC474780
0.7723	Intermediate Similarity	NPC286341
0.7723	Intermediate Similarity	NPC12172
0.7723	Intermediate Similarity	NPC191339
0.7723	Intermediate Similarity	NPC184463
0.7723	Intermediate Similarity	NPC208886
0.7723	Intermediate Similarity	NPC155215
0.77	Intermediate Similarity	NPC283409
0.77	Intermediate Similarity	NPC12872
0.77	Intermediate Similarity	NPC168679
0.7685	Intermediate Similarity	NPC44004
0.7685	Intermediate Similarity	NPC41681
0.7677	Intermediate Similarity	NPC24728
0.767	Intermediate Similarity	NPC93869
0.767	Intermediate Similarity	NPC213698
0.767	Intermediate Similarity	NPC14961
0.767	Intermediate Similarity	NPC170120
0.767	Intermediate Similarity	NPC270013
0.767	Intermediate Similarity	NPC6765
0.7653	Intermediate Similarity	NPC204105
0.7653	Intermediate Similarity	NPC329749
0.7653	Intermediate Similarity	NPC284534
0.7653	Intermediate Similarity	NPC300082
0.7647	Intermediate Similarity	NPC81419
0.7647	Intermediate Similarity	NPC476300
0.7647	Intermediate Similarity	NPC153590
0.7647	Intermediate Similarity	NPC473273
0.7647	Intermediate Similarity	NPC60386
0.7647	Intermediate Similarity	NPC473263
0.7647	Intermediate Similarity	NPC308656
0.7647	Intermediate Similarity	NPC179746
0.7647	Intermediate Similarity	NPC212486
0.7647	Intermediate Similarity	NPC473234
0.7642	Intermediate Similarity	NPC28304
0.7642	Intermediate Similarity	NPC298255
0.7629	Intermediate Similarity	NPC111409
0.7624	Intermediate Similarity	NPC470573
0.7624	Intermediate Similarity	NPC65665
0.7624	Intermediate Similarity	NPC246173
0.7624	Intermediate Similarity	NPC231710
0.7624	Intermediate Similarity	NPC270908
0.7624	Intermediate Similarity	NPC120021
0.7624	Intermediate Similarity	NPC216826
0.7619	Intermediate Similarity	NPC187268
0.76	Intermediate Similarity	NPC202672
0.7596	Intermediate Similarity	NPC76862
0.7596	Intermediate Similarity	NPC39859
0.7596	Intermediate Similarity	NPC470883
0.7596	Intermediate Similarity	NPC158416
0.7596	Intermediate Similarity	NPC476315
0.7593	Intermediate Similarity	NPC203659
0.7593	Intermediate Similarity	NPC474917
0.7593	Intermediate Similarity	NPC86095
0.7593	Intermediate Similarity	NPC100487
0.7576	Intermediate Similarity	NPC64153
0.7576	Intermediate Similarity	NPC162071
0.7573	Intermediate Similarity	NPC474035
0.7573	Intermediate Similarity	NPC262133
0.7573	Intermediate Similarity	NPC470013
0.7573	Intermediate Similarity	NPC470010
0.7573	Intermediate Similarity	NPC127019
0.7573	Intermediate Similarity	NPC81386
0.7573	Intermediate Similarity	NPC323008
0.7573	Intermediate Similarity	NPC274588
0.757	Intermediate Similarity	NPC225353
0.757	Intermediate Similarity	NPC474747
0.757	Intermediate Similarity	NPC13171
0.757	Intermediate Similarity	NPC195510
0.7565	Intermediate Similarity	NPC475309
0.7565	Intermediate Similarity	NPC13710
0.7549	Intermediate Similarity	NPC475881

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 NPC80144 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	2359
0.2-0.3	3924
0.3-0.4	1745
0.4-0.5	519
0.5-0.6	259
0.6-0.7	62
0.7-0.8	2
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
0.7455	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6686	Approved
0.7131	Intermediate Similarity	NPD7507	Approved
0.7115	Intermediate Similarity	NPD6698	Approved
0.7115	Intermediate Similarity	NPD46	Approved
0.7083	Intermediate Similarity	NPD8516	Approved
0.7083	Intermediate Similarity	NPD8517	Approved
0.7083	Intermediate Similarity	NPD8515	Approved
0.7083	Intermediate Similarity	NPD8513	Phase 3
0.7069	Intermediate Similarity	NPD8133	Approved
0.7043	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1695	Approved
0.7009	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.696	Remote Similarity	NPD7319	Approved
0.6957	Remote Similarity	NPD6371	Approved
0.6842	Remote Similarity	NPD6412	Phase 2
0.6818	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7983	Approved
0.6695	Remote Similarity	NPD6053	Discontinued
0.6635	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4249	Approved
0.6557	Remote Similarity	NPD7327	Approved
0.6557	Remote Similarity	NPD7641	Discontinued
0.6557	Remote Similarity	NPD7328	Approved
0.6535	Remote Similarity	NPD8074	Phase 3
0.6532	Remote Similarity	NPD8269	Approved
0.6532	Remote Similarity	NPD8033	Approved
0.6532	Remote Similarity	NPD8266	Approved
0.6532	Remote Similarity	NPD8267	Approved
0.6532	Remote Similarity	NPD8268	Approved
0.6522	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4250	Approved
0.6509	Remote Similarity	NPD4251	Approved
0.6504	Remote Similarity	NPD7516	Approved
0.6484	Remote Similarity	NPD7736	Approved
0.6481	Remote Similarity	NPD7838	Discovery
0.648	Remote Similarity	NPD6370	Approved
0.6452	Remote Similarity	NPD8377	Approved
0.6452	Remote Similarity	NPD8294	Approved
0.6429	Remote Similarity	NPD7829	Approved
0.6429	Remote Similarity	NPD7642	Approved
0.6429	Remote Similarity	NPD7830	Approved
0.6406	Remote Similarity	NPD8293	Discontinued
0.64	Remote Similarity	NPD7503	Approved
0.64	Remote Similarity	NPD8380	Approved
0.64	Remote Similarity	NPD8379	Approved
0.64	Remote Similarity	NPD8335	Approved
0.64	Remote Similarity	NPD8378	Approved
0.64	Remote Similarity	NPD8296	Approved
0.6379	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7492	Approved
0.6372	Remote Similarity	NPD4225	Approved
0.6346	Remote Similarity	NPD6435	Approved
0.6341	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7839	Suspended
0.633	Remote Similarity	NPD5785	Approved
0.6328	Remote Similarity	NPD6616	Approved
0.6328	Remote Similarity	NPD8451	Approved
0.632	Remote Similarity	NPD6054	Approved
0.6303	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD8328	Phase 3
0.6286	Remote Similarity	NPD5362	Discontinued
0.6279	Remote Similarity	NPD7078	Approved
0.6279	Remote Similarity	NPD8448	Approved
0.627	Remote Similarity	NPD6016	Approved
0.627	Remote Similarity	NPD8444	Approved
0.627	Remote Similarity	NPD6015	Approved
0.6262	Remote Similarity	NPD5786	Approved
0.625	Remote Similarity	NPD8299	Approved
0.625	Remote Similarity	NPD8342	Approved
0.625	Remote Similarity	NPD8340	Approved
0.625	Remote Similarity	NPD8341	Approved
0.6222	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5988	Approved
0.6218	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5778	Approved
0.6216	Remote Similarity	NPD5779	Approved
0.621	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6009	Approved
0.619	Remote Similarity	NPD6059	Approved
0.619	Remote Similarity	NPD6319	Approved
0.6174	Remote Similarity	NPD7639	Approved
0.6174	Remote Similarity	NPD7640	Approved
0.6168	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5363	Approved
0.6161	Remote Similarity	NPD5282	Discontinued
0.6154	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5368	Approved
0.6148	Remote Similarity	NPD6882	Approved
0.6136	Remote Similarity	NPD8392	Approved
0.6136	Remote Similarity	NPD8391	Approved
0.6136	Remote Similarity	NPD8390	Approved
0.6132	Remote Similarity	NPD7154	Phase 3
0.6121	Remote Similarity	NPD5344	Discontinued
0.6098	Remote Similarity	NPD4632	Approved
0.6094	Remote Similarity	NPD8080	Discontinued
0.6087	Remote Similarity	NPD7638	Approved
0.608	Remote Similarity	NPD7115	Discovery
0.605	Remote Similarity	NPD6008	Approved
0.6045	Remote Similarity	NPD6845	Suspended
0.6038	Remote Similarity	NPD4270	Approved
0.6038	Remote Similarity	NPD4269	Approved
0.6016	Remote Similarity	NPD8297	Approved
0.6016	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4819	Approved
0.6	Remote Similarity	NPD4820	Approved
0.5985	Remote Similarity	NPD8337	Approved
0.5985	Remote Similarity	NPD8336	Approved
0.597	Remote Similarity	NPD7260	Phase 2
0.5962	Remote Similarity	NPD4802	Phase 2
0.5962	Remote Similarity	NPD4238	Approved
0.5962	Remote Similarity	NPD4268	Approved
0.5962	Remote Similarity	NPD4271	Approved
0.5946	Remote Similarity	NPD6101	Approved
0.5946	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD5369	Approved
0.5943	Remote Similarity	NPD4790	Discontinued
0.5935	Remote Similarity	NPD6649	Approved
0.5935	Remote Similarity	NPD6650	Approved
0.5932	Remote Similarity	NPD8083	Approved
0.5932	Remote Similarity	NPD8139	Approved
0.5932	Remote Similarity	NPD8085	Approved
0.5932	Remote Similarity	NPD8082	Approved
0.5932	Remote Similarity	NPD8084	Approved
0.5932	Remote Similarity	NPD8138	Approved
0.5932	Remote Similarity	NPD8086	Approved
0.5923	Remote Similarity	NPD6067	Discontinued
0.5918	Remote Similarity	NPD898	Approved
0.5918	Remote Similarity	NPD897	Approved
0.5918	Remote Similarity	NPD896	Approved
0.5902	Remote Similarity	NPD6372	Approved
0.5902	Remote Similarity	NPD6373	Approved
0.5902	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8275	Approved
0.5882	Remote Similarity	NPD8276	Approved
0.5868	Remote Similarity	NPD5697	Approved
0.5854	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD4252	Approved
0.5841	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5332	Approved
0.5833	Remote Similarity	NPD5331	Approved
0.5833	Remote Similarity	NPD8081	Approved
0.5833	Remote Similarity	NPD3669	Approved
0.5833	Remote Similarity	NPD8273	Phase 1
0.582	Remote Similarity	NPD6899	Approved
0.582	Remote Similarity	NPD7320	Approved
0.582	Remote Similarity	NPD6881	Approved
0.5809	Remote Similarity	NPD8338	Approved
0.5798	Remote Similarity	NPD7632	Discontinued
0.5794	Remote Similarity	NPD1779	Approved
0.5794	Remote Similarity	NPD1780	Approved
0.5789	Remote Similarity	NPD6399	Phase 3
0.5785	Remote Similarity	NPD6675	Approved
0.5785	Remote Similarity	NPD6402	Approved
0.5785	Remote Similarity	NPD7128	Approved
0.5785	Remote Similarity	NPD8393	Approved
0.5785	Remote Similarity	NPD5739	Approved
0.578	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD6012	Approved
0.5772	Remote Similarity	NPD6014	Approved
0.5772	Remote Similarity	NPD6013	Approved
0.5769	Remote Similarity	NPD6921	Approved
0.5769	Remote Similarity	NPD5983	Phase 2
0.5763	Remote Similarity	NPD6648	Approved
0.5746	Remote Similarity	NPD6033	Approved
0.5738	Remote Similarity	NPD5701	Approved
0.5726	Remote Similarity	NPD7102	Approved
0.5726	Remote Similarity	NPD7290	Approved
0.5726	Remote Similarity	NPD6883	Approved
0.5702	Remote Similarity	NPD8034	Phase 2
0.5702	Remote Similarity	NPD7637	Suspended
0.5702	Remote Similarity	NPD8035	Phase 2
0.5691	Remote Similarity	NPD6011	Approved
0.5682	Remote Similarity	NPD7604	Phase 2
0.568	Remote Similarity	NPD8130	Phase 1
0.568	Remote Similarity	NPD6869	Approved
0.568	Remote Similarity	NPD6617	Approved
0.568	Remote Similarity	NPD6847	Approved
0.5667	Remote Similarity	NPD5211	Phase 2
0.5662	Remote Similarity	NPD5956	Approved
0.566	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD8171	Discontinued
0.5625	Remote Similarity	NPD7524	Approved
0.561	Remote Similarity	NPD8140	Approved
0.561	Remote Similarity	NPD8307	Discontinued
0.561	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.56	Remote Similarity	NPD4634	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