NPASS Compound

Structure

CID124211 OpenBabel06191715482D 37 40 0 0 1 0 0 0 0 0999 V2000 -1.8196 2.4361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1947 4.0904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3789 -2.9603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2539 -2.4550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5338 0.5238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3584 3.2803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8458 4.1239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2223 -0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3780 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6884 0.9742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6899 -1.9501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 2.4364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4964 3.1629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 1.4621 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8451 -1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5344 -1.4622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2225 -1.4617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6881 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3589 4.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6890 0.9752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8442 1.4626 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3786 -1.9496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5341 -0.4869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9747 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 2.4504 2.9604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0232 -1.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0911 -1.9627 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3970 -0.7097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6154 4.9681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 5.8114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5573 1.4768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8440 2.4379 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 27 1 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 1 1 6 0 0 0 14 16 1 0 0 0 0 15 30 2 0 0 0 0 15 37 1 0 0 0 0 16 28 1 6 0 0 0 17 22 1 0 0 0 0 17 31 2 0 0 0 0 18 26 1 0 0 0 0 18 27 1 6 0 0 0 19 26 1 0 0 0 0 19 32 2 0 0 0 0 20 29 1 0 0 0 0 20 33 2 0 0 0 0 21 34 2 0 0 0 0 21 35 1 0 0 0 0 22 23 2 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 36 2 0 0 0 0 25 28 1 6 0 0 0 25 37 1 0 0 0 0 27 5 1 6 0 0 0 28 29 1 6 0 0 0 29 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.26
Volume:	527.781
LogP:	2.698
LogD:	1.728
LogS:	-4.401
# Rotatable Bonds:	6
TPSA:	131.88
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	4.993
Fsp3:	0.724
Lipinski Rule-of-5:	Accepted
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:	-5.378
MDCK Permeability:	2.3056021746015176e-05
Pgp-inhibitor:	0.641
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.229
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.353
Plasma Protein Binding (PPB):	79.38726043701172%
Volume Distribution (VD):	0.296
Pgp-substrate:	17.194887161254883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.497
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.833
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.087
CYP3A4-substrate:	0.517

ADMET: Excretion

Clearance (CL):	3.613
Half-life (T1/2):	0.852

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.154
Drug-inuced Liver Injury (DILI):	0.309
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.25
Skin Sensitization:	0.094
Carcinogencity:	0.045
Eye Corrosion:	0.018
Eye Irritation:	0.025
Respiratory Toxicity:	0.422

Download Data

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

Natural Product: NPC124211

Natural Product ID:	NPC124211
*Common Name:**	Lucidenic Acid D2
IUPAC Name:	(4R)-4-[(5R,10S,12S,13R,14R,17R)-12-acetyloxy-4,4,10,13,14-pentamethyl-3,7,11,15-tetraoxo-2,5,6,12,16,17-hexahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Synonyms:	Lucidenic Acid D2
Standard InCHIKey:	LTJSBYAKDOGXLX-JTJCPSTFSA-N
Standard InCHI:	InChI=1S/C29H38O8/c1-14(8-9-21(34)35)16-12-20(33)29(7)22-17(31)13-18-26(3,4)19(32)10-11-27(18,5)23(22)24(36)25(28(16,29)6)37-15(2)30/h14,16,18,25H,8-13H2,1-7H3,(H,34,35)/p-1/t14-,16-,18+,25-,27+,28+,29+/m1/s1
SMILES:	C[C@H](CCC(=O)[O-])[C@H]1CC(=O)[C@@]2(C)C3=C(C(=O)[C@H]([C@]12C)OC(=O)C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518100
PubChem CID:	23247891
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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	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	1
Others	5

Activity Type	# Activity
Cell Line	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[508830]
NPT2	Others	Unspecified		Activity	=	2.0	%	PMID[508830]
NPT2	Others	Unspecified		Activity	=	26.1	%	PMID[508830]
NPT2	Others	Unspecified		Activity	=	73.8	%	PMID[508830]
NPT2	Others	Unspecified		Activity	=	96.1	%	PMID[508830]
NPT2	Others	Unspecified		IC50	=	287.0	molar ratio	PMID[508830]

☑ 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 NPC124211 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	207
0.1-0.2	1508
0.2-0.3	6370
0.3-0.4	12970
0.4-0.5	8731
0.5-0.6	7091
0.6-0.7	4758
0.7-0.8	914
0.8-0.85	91
0.85-0.9	37
0.9-0.95	13
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC53222
0.9789	High Similarity	NPC33973
0.9789	High Similarity	NPC70967
0.9688	High Similarity	NPC135854
0.9688	High Similarity	NPC2436
0.9688	High Similarity	NPC216245
0.9688	High Similarity	NPC470251
0.9677	High Similarity	NPC216904
0.9574	High Similarity	NPC275439
0.9574	High Similarity	NPC112753
0.9474	High Similarity	NPC88198
0.9474	High Similarity	NPC157787
0.9118	High Similarity	NPC115303
0.9109	High Similarity	NPC286174
0.9109	High Similarity	NPC77947
0.9062	High Similarity	NPC43747
0.9053	High Similarity	NPC255809
0.902	High Similarity	NPC129689
0.9	High Similarity	NPC51452
0.8958	High Similarity	NPC125622
0.8942	High Similarity	NPC472929
0.8854	High Similarity	NPC241156
0.8824	High Similarity	NPC295244
0.88	High Similarity	NPC251017
0.8763	High Similarity	NPC305483
0.8763	High Similarity	NPC95565
0.8763	High Similarity	NPC96859
0.8763	High Similarity	NPC328162
0.8673	High Similarity	NPC23680
0.8673	High Similarity	NPC106557
0.8673	High Similarity	NPC121339
0.866	High Similarity	NPC470016
0.866	High Similarity	NPC317586
0.8654	High Similarity	NPC473036
0.8654	High Similarity	NPC272898
0.8646	High Similarity	NPC25750
0.8571	High Similarity	NPC243525
0.8571	High Similarity	NPC3772
0.8571	High Similarity	NPC40765
0.8557	High Similarity	NPC166906
0.8557	High Similarity	NPC477439
0.8544	High Similarity	NPC473037
0.8519	High Similarity	NPC472927
0.8519	High Similarity	NPC472934
0.8515	High Similarity	NPC281702
0.85	High Similarity	NPC144660
0.85	High Similarity	NPC299971
0.85	High Similarity	NPC307954
0.8495	Intermediate Similarity	NPC473038
0.8469	Intermediate Similarity	NPC477438
0.8469	Intermediate Similarity	NPC37646
0.8469	Intermediate Similarity	NPC477437
0.84	Intermediate Similarity	NPC16021
0.8396	Intermediate Similarity	NPC472928
0.8387	Intermediate Similarity	NPC209882
0.8367	Intermediate Similarity	NPC184870
0.8364	Intermediate Similarity	NPC472933
0.835	Intermediate Similarity	NPC28656
0.8333	Intermediate Similarity	NPC308726
0.8333	Intermediate Similarity	NPC56498
0.8333	Intermediate Similarity	NPC119601
0.8333	Intermediate Similarity	NPC473039
0.8318	Intermediate Similarity	NPC264634
0.8318	Intermediate Similarity	NPC147180
0.8317	Intermediate Similarity	NPC316964
0.8317	Intermediate Similarity	NPC205899
0.8317	Intermediate Similarity	NPC51370
0.83	Intermediate Similarity	NPC226986
0.83	Intermediate Similarity	NPC122294
0.8283	Intermediate Similarity	NPC473648
0.828	Intermediate Similarity	NPC469561
0.828	Intermediate Similarity	NPC271784
0.8265	Intermediate Similarity	NPC470254
0.8265	Intermediate Similarity	NPC477435
0.8265	Intermediate Similarity	NPC477436
0.8252	Intermediate Similarity	NPC55872
0.8247	Intermediate Similarity	NPC20388
0.8241	Intermediate Similarity	NPC472926
0.8235	Intermediate Similarity	NPC473514
0.8235	Intermediate Similarity	NPC302537
0.8235	Intermediate Similarity	NPC163372
0.8218	Intermediate Similarity	NPC10364
0.82	Intermediate Similarity	NPC7124
0.82	Intermediate Similarity	NPC328371
0.8163	Intermediate Similarity	NPC26888
0.8163	Intermediate Similarity	NPC107690
0.8163	Intermediate Similarity	NPC297265
0.8155	Intermediate Similarity	NPC80781
0.8155	Intermediate Similarity	NPC234892
0.8144	Intermediate Similarity	NPC474889
0.8137	Intermediate Similarity	NPC327431
0.8137	Intermediate Similarity	NPC476274
0.8137	Intermediate Similarity	NPC287833
0.8131	Intermediate Similarity	NPC470496
0.8119	Intermediate Similarity	NPC18319
0.8105	Intermediate Similarity	NPC123319
0.8105	Intermediate Similarity	NPC94531
0.8105	Intermediate Similarity	NPC311702
0.81	Intermediate Similarity	NPC174948
0.81	Intermediate Similarity	NPC173875
0.81	Intermediate Similarity	NPC469995
0.81	Intermediate Similarity	NPC318282
0.81	Intermediate Similarity	NPC297199
0.81	Intermediate Similarity	NPC469599
0.8095	Intermediate Similarity	NPC475494
0.8095	Intermediate Similarity	NPC181357
0.8091	Intermediate Similarity	NPC270958
0.8077	Intermediate Similarity	NPC275583
0.8077	Intermediate Similarity	NPC236390
0.8073	Intermediate Similarity	NPC202889
0.8061	Intermediate Similarity	NPC111585
0.8061	Intermediate Similarity	NPC148414
0.8061	Intermediate Similarity	NPC175628
0.8058	Intermediate Similarity	NPC476240
0.8058	Intermediate Similarity	NPC476223
0.8058	Intermediate Similarity	NPC224720
0.8056	Intermediate Similarity	NPC43775
0.8056	Intermediate Similarity	NPC34315
0.8041	Intermediate Similarity	NPC185059
0.8041	Intermediate Similarity	NPC475001
0.8041	Intermediate Similarity	NPC242864
0.8041	Intermediate Similarity	NPC143767
0.8041	Intermediate Similarity	NPC131470
0.8037	Intermediate Similarity	NPC304495
0.802	Intermediate Similarity	NPC42042
0.802	Intermediate Similarity	NPC192428
0.8019	Intermediate Similarity	NPC475294
0.8019	Intermediate Similarity	NPC220974
0.8019	Intermediate Similarity	NPC472925
0.8019	Intermediate Similarity	NPC44063
0.8	Intermediate Similarity	NPC159410
0.8	Intermediate Similarity	NPC109512
0.8	Intermediate Similarity	NPC235889
0.8	Intermediate Similarity	NPC320801
0.8	Intermediate Similarity	NPC96268
0.7982	Intermediate Similarity	NPC71348
0.7982	Intermediate Similarity	NPC285956
0.7982	Intermediate Similarity	NPC221144
0.7982	Intermediate Similarity	NPC100267
0.7982	Intermediate Similarity	NPC170487
0.7982	Intermediate Similarity	NPC475524
0.7981	Intermediate Similarity	NPC195290
0.7981	Intermediate Similarity	NPC204450
0.7981	Intermediate Similarity	NPC475558
0.7981	Intermediate Similarity	NPC136289
0.7981	Intermediate Similarity	NPC163249
0.7981	Intermediate Similarity	NPC473788
0.7981	Intermediate Similarity	NPC293753
0.798	Intermediate Similarity	NPC168027
0.798	Intermediate Similarity	NPC248913
0.798	Intermediate Similarity	NPC150383
0.798	Intermediate Similarity	NPC185936
0.7961	Intermediate Similarity	NPC472972
0.7959	Intermediate Similarity	NPC275740
0.7959	Intermediate Similarity	NPC86319
0.7946	Intermediate Similarity	NPC118638
0.7941	Intermediate Similarity	NPC320306
0.7941	Intermediate Similarity	NPC292133
0.7938	Intermediate Similarity	NPC99909
0.7925	Intermediate Similarity	NPC196528
0.7925	Intermediate Similarity	NPC181265
0.7921	Intermediate Similarity	NPC200702
0.7921	Intermediate Similarity	NPC184848
0.7921	Intermediate Similarity	NPC69548
0.7921	Intermediate Similarity	NPC48330
0.7917	Intermediate Similarity	NPC11711
0.7917	Intermediate Similarity	NPC90287
0.7905	Intermediate Similarity	NPC159442
0.7905	Intermediate Similarity	NPC264048
0.79	Intermediate Similarity	NPC79117
0.79	Intermediate Similarity	NPC109414
0.79	Intermediate Similarity	NPC170220
0.79	Intermediate Similarity	NPC206810
0.79	Intermediate Similarity	NPC107674
0.79	Intermediate Similarity	NPC141497
0.7895	Intermediate Similarity	NPC168188
0.7895	Intermediate Similarity	NPC470015
0.789	Intermediate Similarity	NPC231589
0.789	Intermediate Similarity	NPC118860
0.789	Intermediate Similarity	NPC214797
0.7885	Intermediate Similarity	NPC81530
0.7879	Intermediate Similarity	NPC289213
0.7879	Intermediate Similarity	NPC183283
0.7879	Intermediate Similarity	NPC471896
0.787	Intermediate Similarity	NPC241927
0.787	Intermediate Similarity	NPC250018
0.787	Intermediate Similarity	NPC2766
0.787	Intermediate Similarity	NPC258543
0.7864	Intermediate Similarity	NPC114274
0.7864	Intermediate Similarity	NPC197386
0.7864	Intermediate Similarity	NPC147954
0.7857	Intermediate Similarity	NPC471722
0.7857	Intermediate Similarity	NPC471854
0.7843	Intermediate Similarity	NPC120708
0.7843	Intermediate Similarity	NPC173272
0.7843	Intermediate Similarity	NPC472941
0.7843	Intermediate Similarity	NPC456
0.7835	Intermediate Similarity	NPC28252
0.7835	Intermediate Similarity	NPC55309
0.7835	Intermediate Similarity	NPC229717

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 NPC124211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1958
0.2-0.3	4033
0.3-0.4	1983
0.4-0.5	561
0.5-0.6	183
0.6-0.7	148
0.7-0.8	96
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8558	High Similarity	NPD6373	Approved
0.8558	High Similarity	NPD6372	Approved
0.8396	Intermediate Similarity	NPD6649	Approved
0.8396	Intermediate Similarity	NPD6650	Approved
0.8269	Intermediate Similarity	NPD6675	Approved
0.8269	Intermediate Similarity	NPD7128	Approved
0.8269	Intermediate Similarity	NPD5739	Approved
0.8269	Intermediate Similarity	NPD6402	Approved
0.8265	Intermediate Similarity	NPD6399	Phase 3
0.8218	Intermediate Similarity	NPD5696	Approved
0.8113	Intermediate Similarity	NPD6881	Approved
0.8113	Intermediate Similarity	NPD7320	Approved
0.8113	Intermediate Similarity	NPD6899	Approved
0.81	Intermediate Similarity	NPD5695	Phase 3
0.8041	Intermediate Similarity	NPD6672	Approved
0.8041	Intermediate Similarity	NPD5737	Approved
0.802	Intermediate Similarity	NPD4697	Phase 3
0.8019	Intermediate Similarity	NPD5701	Approved
0.8019	Intermediate Similarity	NPD5697	Approved
0.7982	Intermediate Similarity	NPD8297	Approved
0.7982	Intermediate Similarity	NPD6882	Approved
0.7963	Intermediate Similarity	NPD7102	Approved
0.7963	Intermediate Similarity	NPD6883	Approved
0.7963	Intermediate Similarity	NPD7290	Approved
0.7944	Intermediate Similarity	NPD6011	Approved
0.7941	Intermediate Similarity	NPD6084	Phase 2
0.7941	Intermediate Similarity	NPD6083	Phase 2
0.789	Intermediate Similarity	NPD6617	Approved
0.789	Intermediate Similarity	NPD6869	Approved
0.789	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD8130	Phase 1
0.789	Intermediate Similarity	NPD6847	Approved
0.787	Intermediate Similarity	NPD6013	Approved
0.787	Intermediate Similarity	NPD6012	Approved
0.787	Intermediate Similarity	NPD6014	Approved
0.7778	Intermediate Similarity	NPD5328	Approved
0.767	Intermediate Similarity	NPD5221	Approved
0.767	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD5222	Approved
0.7624	Intermediate Similarity	NPD6050	Approved
0.7624	Intermediate Similarity	NPD6079	Approved
0.7611	Intermediate Similarity	NPD6868	Approved
0.76	Intermediate Similarity	NPD6904	Approved
0.76	Intermediate Similarity	NPD6080	Approved
0.76	Intermediate Similarity	NPD6673	Approved
0.7596	Intermediate Similarity	NPD4755	Approved
0.7596	Intermediate Similarity	NPD5173	Approved
0.7596	Intermediate Similarity	NPD7902	Approved
0.7525	Intermediate Similarity	NPD5692	Phase 3
0.7478	Intermediate Similarity	NPD6335	Approved
0.7476	Intermediate Similarity	NPD7748	Approved
0.7475	Intermediate Similarity	NPD7146	Approved
0.7475	Intermediate Similarity	NPD5279	Phase 3
0.7475	Intermediate Similarity	NPD7521	Approved
0.7475	Intermediate Similarity	NPD7334	Approved
0.7475	Intermediate Similarity	NPD6409	Approved
0.7475	Intermediate Similarity	NPD3618	Phase 1
0.7475	Intermediate Similarity	NPD6684	Approved
0.7475	Intermediate Similarity	NPD5330	Approved
0.7456	Intermediate Similarity	NPD6274	Approved
0.7453	Intermediate Similarity	NPD5285	Approved
0.7453	Intermediate Similarity	NPD5286	Approved
0.7453	Intermediate Similarity	NPD4700	Approved
0.7453	Intermediate Similarity	NPD4696	Approved
0.7451	Intermediate Similarity	NPD8035	Phase 2
0.7451	Intermediate Similarity	NPD8034	Phase 2
0.7451	Intermediate Similarity	NPD5694	Approved
0.7449	Intermediate Similarity	NPD4786	Approved
0.7431	Intermediate Similarity	NPD6008	Approved
0.7414	Intermediate Similarity	NPD7101	Approved
0.7414	Intermediate Similarity	NPD7100	Approved
0.7404	Intermediate Similarity	NPD5210	Approved
0.7404	Intermediate Similarity	NPD4629	Approved
0.7391	Intermediate Similarity	NPD6317	Approved
0.7383	Intermediate Similarity	NPD5223	Approved
0.7368	Intermediate Similarity	NPD3617	Approved
0.735	Intermediate Similarity	NPD6319	Approved
0.7328	Intermediate Similarity	NPD6313	Approved
0.7328	Intermediate Similarity	NPD6314	Approved
0.7327	Intermediate Similarity	NPD6903	Approved
0.7327	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5226	Approved
0.7315	Intermediate Similarity	NPD5225	Approved
0.7315	Intermediate Similarity	NPD4633	Approved
0.7315	Intermediate Similarity	NPD5224	Approved
0.7315	Intermediate Similarity	NPD5211	Phase 2
0.7308	Intermediate Similarity	NPD7900	Approved
0.7308	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6098	Approved
0.7288	Intermediate Similarity	NPD6908	Approved
0.7288	Intermediate Similarity	NPD6909	Approved
0.7282	Intermediate Similarity	NPD5281	Approved
0.7282	Intermediate Similarity	NPD7515	Phase 2
0.7282	Intermediate Similarity	NPD5693	Phase 1
0.7282	Intermediate Similarity	NPD5284	Approved
0.7281	Intermediate Similarity	NPD4632	Approved
0.7273	Intermediate Similarity	NPD4767	Approved
0.7273	Intermediate Similarity	NPD4768	Approved
0.7255	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4753	Phase 2
0.7248	Intermediate Similarity	NPD5175	Approved
0.7248	Intermediate Similarity	NPD4754	Approved
0.7248	Intermediate Similarity	NPD5174	Approved
0.7245	Intermediate Similarity	NPD3667	Approved
0.7241	Intermediate Similarity	NPD6009	Approved
0.7238	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5654	Approved
0.72	Intermediate Similarity	NPD5329	Approved
0.7182	Intermediate Similarity	NPD5141	Approved
0.7167	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD5983	Phase 2
0.7143	Intermediate Similarity	NPD4729	Approved
0.7143	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4694	Approved
0.7129	Intermediate Similarity	NPD5690	Phase 2
0.7129	Intermediate Similarity	NPD5280	Approved
0.7115	Intermediate Similarity	NPD6411	Approved
0.7107	Intermediate Similarity	NPD7492	Approved
0.7103	Intermediate Similarity	NPD5959	Approved
0.71	Intermediate Similarity	NPD4197	Approved
0.71	Intermediate Similarity	NPD3665	Phase 1
0.71	Intermediate Similarity	NPD3133	Approved
0.71	Intermediate Similarity	NPD3666	Approved
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD6059	Approved
0.7059	Intermediate Similarity	NPD6054	Approved
0.7054	Intermediate Similarity	NPD6614	Approved
0.7049	Intermediate Similarity	NPD6336	Discontinued
0.7049	Intermediate Similarity	NPD6616	Approved
0.7048	Intermediate Similarity	NPD4202	Approved
0.7037	Intermediate Similarity	NPD7638	Approved
0.703	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5207	Approved
0.7018	Intermediate Similarity	NPD5249	Phase 3
0.7018	Intermediate Similarity	NPD5250	Approved
0.7018	Intermediate Similarity	NPD5251	Approved
0.7018	Intermediate Similarity	NPD5247	Approved
0.7018	Intermediate Similarity	NPD5248	Approved
0.6992	Remote Similarity	NPD7078	Approved
0.6992	Remote Similarity	NPD8293	Discontinued
0.6991	Remote Similarity	NPD5168	Approved
0.6991	Remote Similarity	NPD5128	Approved
0.6972	Remote Similarity	NPD7640	Approved
0.6972	Remote Similarity	NPD7639	Approved
0.6961	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6370	Approved
0.6935	Remote Similarity	NPD7736	Approved
0.6931	Remote Similarity	NPD3668	Phase 3
0.693	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6101	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7260	Phase 2
0.69	Remote Similarity	NPD4221	Approved
0.69	Remote Similarity	NPD4223	Phase 3
0.6893	Remote Similarity	NPD3573	Approved
0.6885	Remote Similarity	NPD8328	Phase 3
0.687	Remote Similarity	NPD5135	Approved
0.687	Remote Similarity	NPD4634	Approved
0.687	Remote Similarity	NPD5169	Approved
0.687	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4695	Discontinued
0.686	Remote Similarity	NPD6015	Approved
0.686	Remote Similarity	NPD6016	Approved
0.6852	Remote Similarity	NPD7614	Phase 1
0.685	Remote Similarity	NPD6845	Suspended
0.6847	Remote Similarity	NPD7632	Discontinued
0.6827	Remote Similarity	NPD5208	Approved
0.6822	Remote Similarity	NPD6001	Approved
0.681	Remote Similarity	NPD5217	Approved
0.681	Remote Similarity	NPD5215	Approved
0.681	Remote Similarity	NPD5216	Approved
0.681	Remote Similarity	NPD5127	Approved
0.6804	Remote Similarity	NPD6117	Approved
0.6803	Remote Similarity	NPD5988	Approved
0.68	Remote Similarity	NPD4692	Approved
0.68	Remote Similarity	NPD4139	Approved
0.6771	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6081	Approved
0.6735	Remote Similarity	NPD6116	Phase 1
0.6729	Remote Similarity	NPD5133	Approved
0.6699	Remote Similarity	NPD1694	Approved
0.6697	Remote Similarity	NPD7732	Phase 3
0.6696	Remote Similarity	NPD5091	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6639	Remote Similarity	NPD5167	Approved
0.6635	Remote Similarity	NPD4689	Approved
0.6635	Remote Similarity	NPD4138	Approved
0.6635	Remote Similarity	NPD4688	Approved
0.6635	Remote Similarity	NPD4690	Approved
0.6635	Remote Similarity	NPD4693	Phase 3
0.6635	Remote Similarity	NPD5205	Approved
0.661	Remote Similarity	NPD6053	Discontinued
0.6609	Remote Similarity	NPD6412	Phase 2

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