NPASS Compound

Structure

CID99909 OpenBabel06191715442D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.0017 2.9229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3779 -2.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2526 -2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0202 6.2005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5069 5.3569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 0.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 2.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6890 3.8964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6879 0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6885 0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2210 -0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3770 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8440 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6894 -1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 2.4357 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8448 1.4617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6888 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 -1.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5336 -1.4618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2212 -1.4613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5327 4.3832 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8445 -0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3776 -1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5329 5.3572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5333 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9744 0.0000 C 0 0 1 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 -0.0211 -1.9625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0875 -1.9609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3760 3.8959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6896 5.8444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 24 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 1 1 1 0 0 0 18 19 1 0 0 0 0 19 29 1 6 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 25 1 0 0 0 0 21 31 2 0 0 0 0 22 26 1 0 0 0 0 22 28 1 6 0 0 0 23 26 1 0 0 0 0 23 32 2 0 0 0 0 24 27 1 0 0 0 0 24 33 1 6 0 0 0 25 30 1 0 0 0 0 27 34 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	4.681
LogD:	4.345
LogS:	-4.709
# Rotatable Bonds:	5
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	4.81
Fsp3:	0.867
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:	-5.051
MDCK Permeability:	1.4798851225350518e-05
Pgp-inhibitor:	0.872
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	90.57472229003906%
Volume Distribution (VD):	0.924
Pgp-substrate:	2.8144097328186035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.453
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.951
CYP2C9-inhibitor:	0.291
CYP2C9-substrate:	0.289
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.574
CYP3A4-substrate:	0.835

ADMET: Excretion

Clearance (CL):	5.987
Half-life (T1/2):	0.335

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.52
Maximum Recommended Daily Dose:	0.852
Skin Sensitization:	0.125
Carcinogencity:	0.077
Eye Corrosion:	0.005
Eye Irritation:	0.018
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC99909

Natural Product ID:	NPC99909
*Common Name:**	Lucidumol A
IUPAC Name:	(5R,10S,13R,14R,17R)-17-[(2R,5S)-5,6-dihydroxy-6-methylheptan-2-yl]-4,4,10,13,14-pentamethyl-2,5,6,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,7-dione
Synonyms:	Lucidumol A
Standard InCHIKey:	LVGCWXNRZNCAJG-AMKDLFIQSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-18(9-10-24(33)27(4,5)34)19-11-16-30(8)25-20(12-15-29(19,30)7)28(6)14-13-23(32)26(2,3)22(28)17-21(25)31/h18-19,22,24,33-34H,9-17H2,1-8H3/t18-,19-,22+,24+,28-,29-,30+/m1/s1
SMILES:	C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2C(=O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)CC[C@@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1917739
PubChem CID:	475410
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
EC50	1
ED50	2
IC50	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	2
PROTEIN COMPLEX	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	11000.0	nM	PMID[454075]
NPT22802	PROTEIN COMPLEX	Bile acid receptor/Retinoic acid receptor RXR-alpha	Mus musculus	EC50	>	18600.0	nM	PMID[454074]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.3	ug ml-1	PMID[454075]

☑ 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 NPC99909 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	1404
0.2-0.3	6336
0.3-0.4	15390
0.4-0.5	6791
0.5-0.6	7212
0.6-0.7	4284
0.7-0.8	915
0.8-0.85	153
0.85-0.9	31
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC318332
0.9059	High Similarity	NPC138756
0.8953	High Similarity	NPC44181
0.8941	High Similarity	NPC89077
0.8929	High Similarity	NPC473246
0.8837	High Similarity	NPC90652
0.8778	High Similarity	NPC200702
0.875	High Similarity	NPC136801
0.875	High Similarity	NPC289213
0.8736	High Similarity	NPC470417
0.8721	High Similarity	NPC72133
0.8706	High Similarity	NPC214043
0.8706	High Similarity	NPC85774
0.8652	High Similarity	NPC19114
0.8636	High Similarity	NPC32830
0.8605	High Similarity	NPC473038
0.8588	High Similarity	NPC86370
0.8571	High Similarity	NPC255809
0.8571	High Similarity	NPC297199
0.8571	High Similarity	NPC37646
0.8571	High Similarity	NPC241156
0.8523	High Similarity	NPC131470
0.8523	High Similarity	NPC143767
0.8523	High Similarity	NPC471722
0.8506	High Similarity	NPC474778
0.8506	High Similarity	NPC474733
0.8506	High Similarity	NPC118648
0.8506	High Similarity	NPC145879
0.8506	High Similarity	NPC473168
0.8506	High Similarity	NPC475022
0.8506	High Similarity	NPC31564
0.8506	High Similarity	NPC474732
0.8506	High Similarity	NPC222613
0.8488	Intermediate Similarity	NPC209882
0.8478	Intermediate Similarity	NPC3772
0.8478	Intermediate Similarity	NPC243525
0.8478	Intermediate Similarity	NPC125622
0.8478	Intermediate Similarity	NPC472941
0.8478	Intermediate Similarity	NPC456
0.8478	Intermediate Similarity	NPC473164
0.8478	Intermediate Similarity	NPC40765
0.8427	Intermediate Similarity	NPC477943
0.8427	Intermediate Similarity	NPC1015
0.8427	Intermediate Similarity	NPC31985
0.8427	Intermediate Similarity	NPC275740
0.8427	Intermediate Similarity	NPC77263
0.8427	Intermediate Similarity	NPC86319
0.8427	Intermediate Similarity	NPC250592
0.8409	Intermediate Similarity	NPC475740
0.8409	Intermediate Similarity	NPC136548
0.8409	Intermediate Similarity	NPC58063
0.8404	Intermediate Similarity	NPC316964
0.8395	Intermediate Similarity	NPC470299
0.8391	Intermediate Similarity	NPC469948
0.8391	Intermediate Similarity	NPC94531
0.8391	Intermediate Similarity	NPC123319
0.8391	Intermediate Similarity	NPC311702
0.8391	Intermediate Similarity	NPC197823
0.8391	Intermediate Similarity	NPC474083
0.8387	Intermediate Similarity	NPC473161
0.8387	Intermediate Similarity	NPC122294
0.8387	Intermediate Similarity	NPC43747
0.8387	Intermediate Similarity	NPC106557
0.8387	Intermediate Similarity	NPC121339
0.8372	Intermediate Similarity	NPC271784
0.8352	Intermediate Similarity	NPC25750
0.8352	Intermediate Similarity	NPC472930
0.8352	Intermediate Similarity	NPC233118
0.8352	Intermediate Similarity	NPC474736
0.8333	Intermediate Similarity	NPC191684
0.8333	Intermediate Similarity	NPC183283
0.8333	Intermediate Similarity	NPC472490
0.8315	Intermediate Similarity	NPC471724
0.8298	Intermediate Similarity	NPC16021
0.8298	Intermediate Similarity	NPC147954
0.828	Intermediate Similarity	NPC249954
0.828	Intermediate Similarity	NPC471463
0.8276	Intermediate Similarity	NPC329043
0.8276	Intermediate Similarity	NPC59453
0.8276	Intermediate Similarity	NPC237712
0.8276	Intermediate Similarity	NPC227064
0.8276	Intermediate Similarity	NPC58841
0.8276	Intermediate Similarity	NPC321187
0.8276	Intermediate Similarity	NPC82902
0.8276	Intermediate Similarity	NPC221758
0.8276	Intermediate Similarity	NPC161423
0.8261	Intermediate Similarity	NPC166906
0.8261	Intermediate Similarity	NPC8993
0.8261	Intermediate Similarity	NPC473172
0.8261	Intermediate Similarity	NPC184870
0.8261	Intermediate Similarity	NPC174051
0.8261	Intermediate Similarity	NPC67831
0.8256	Intermediate Similarity	NPC469325
0.8242	Intermediate Similarity	NPC63748
0.8242	Intermediate Similarity	NPC475806
0.8242	Intermediate Similarity	NPC473998
0.8242	Intermediate Similarity	NPC155304
0.8242	Intermediate Similarity	NPC233116
0.8242	Intermediate Similarity	NPC262870
0.8229	Intermediate Similarity	NPC473424
0.8222	Intermediate Similarity	NPC26959
0.8222	Intermediate Similarity	NPC186688
0.8222	Intermediate Similarity	NPC215029
0.8222	Intermediate Similarity	NPC473999
0.8222	Intermediate Similarity	NPC326627
0.8222	Intermediate Similarity	NPC309603
0.8222	Intermediate Similarity	NPC268406
0.8222	Intermediate Similarity	NPC54689
0.8222	Intermediate Similarity	NPC476733
0.8222	Intermediate Similarity	NPC214387
0.8222	Intermediate Similarity	NPC474245
0.8222	Intermediate Similarity	NPC310010
0.8211	Intermediate Similarity	NPC51370
0.8211	Intermediate Similarity	NPC144660
0.8211	Intermediate Similarity	NPC88198
0.8211	Intermediate Similarity	NPC299971
0.8211	Intermediate Similarity	NPC287833
0.8211	Intermediate Similarity	NPC157787
0.8211	Intermediate Similarity	NPC307954
0.8202	Intermediate Similarity	NPC241875
0.8202	Intermediate Similarity	NPC317590
0.8202	Intermediate Similarity	NPC469317
0.8202	Intermediate Similarity	NPC469314
0.8202	Intermediate Similarity	NPC93778
0.8191	Intermediate Similarity	NPC472073
0.8191	Intermediate Similarity	NPC472074
0.8182	Intermediate Similarity	NPC472940
0.8182	Intermediate Similarity	NPC470574
0.8182	Intermediate Similarity	NPC471224
0.8182	Intermediate Similarity	NPC474218
0.8182	Intermediate Similarity	NPC472931
0.8172	Intermediate Similarity	NPC318282
0.8172	Intermediate Similarity	NPC469995
0.8172	Intermediate Similarity	NPC259286
0.8172	Intermediate Similarity	NPC174948
0.8172	Intermediate Similarity	NPC317586
0.8172	Intermediate Similarity	NPC472932
0.8172	Intermediate Similarity	NPC473170
0.8172	Intermediate Similarity	NPC173875
0.8172	Intermediate Similarity	NPC470016
0.8161	Intermediate Similarity	NPC41539
0.8161	Intermediate Similarity	NPC168188
0.8161	Intermediate Similarity	NPC469561
0.8161	Intermediate Similarity	NPC470015
0.8152	Intermediate Similarity	NPC250575
0.8152	Intermediate Similarity	NPC474807
0.8152	Intermediate Similarity	NPC243866
0.8152	Intermediate Similarity	NPC475255
0.8152	Intermediate Similarity	NPC69454
0.8148	Intermediate Similarity	NPC223187
0.8144	Intermediate Similarity	NPC239716
0.8132	Intermediate Similarity	NPC129913
0.8132	Intermediate Similarity	NPC469400
0.8132	Intermediate Similarity	NPC320026
0.8132	Intermediate Similarity	NPC477149
0.8132	Intermediate Similarity	NPC48010
0.8132	Intermediate Similarity	NPC477147
0.8132	Intermediate Similarity	NPC171441
0.8111	Intermediate Similarity	NPC242864
0.8111	Intermediate Similarity	NPC328539
0.8095	Intermediate Similarity	NPC325946
0.809	Intermediate Similarity	NPC327115
0.809	Intermediate Similarity	NPC472494
0.809	Intermediate Similarity	NPC55309
0.809	Intermediate Similarity	NPC28252
0.809	Intermediate Similarity	NPC158393
0.809	Intermediate Similarity	NPC94755
0.809	Intermediate Similarity	NPC472491
0.809	Intermediate Similarity	NPC51014
0.809	Intermediate Similarity	NPC469994
0.8085	Intermediate Similarity	NPC96859
0.8085	Intermediate Similarity	NPC305483
0.8085	Intermediate Similarity	NPC328162
0.8085	Intermediate Similarity	NPC7124
0.8085	Intermediate Similarity	NPC95565
0.8085	Intermediate Similarity	NPC328371
0.8085	Intermediate Similarity	NPC117133
0.8068	Intermediate Similarity	NPC472265
0.8068	Intermediate Similarity	NPC320801
0.8065	Intermediate Similarity	NPC196485
0.8065	Intermediate Similarity	NPC111015
0.8065	Intermediate Similarity	NPC245972
0.8046	Intermediate Similarity	NPC193347
0.8046	Intermediate Similarity	NPC151519
0.8046	Intermediate Similarity	NPC212083
0.8043	Intermediate Similarity	NPC107690
0.8043	Intermediate Similarity	NPC168027
0.8043	Intermediate Similarity	NPC185936
0.8043	Intermediate Similarity	NPC272746
0.8043	Intermediate Similarity	NPC189520
0.8043	Intermediate Similarity	NPC150383
0.8041	Intermediate Similarity	NPC477915
0.8041	Intermediate Similarity	NPC234892
0.8041	Intermediate Similarity	NPC293753
0.8041	Intermediate Similarity	NPC281702
0.8023	Intermediate Similarity	NPC2482
0.8023	Intermediate Similarity	NPC22403
0.8023	Intermediate Similarity	NPC472478
0.8022	Intermediate Similarity	NPC2983
0.8022	Intermediate Similarity	NPC76879

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 NPC99909 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1919
0.2-0.3	4234
0.3-0.4	1982
0.4-0.5	436
0.5-0.6	143
0.6-0.7	180
0.7-0.8	96
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8295	Intermediate Similarity	NPD5279	Phase 3
0.8276	Intermediate Similarity	NPD3666	Approved
0.8276	Intermediate Similarity	NPD3133	Approved
0.8276	Intermediate Similarity	NPD3665	Phase 1
0.8276	Intermediate Similarity	NPD4786	Approved
0.8222	Intermediate Similarity	NPD4753	Phase 2
0.8222	Intermediate Similarity	NPD5328	Approved
0.8172	Intermediate Similarity	NPD5210	Approved
0.8172	Intermediate Similarity	NPD4629	Approved
0.809	Intermediate Similarity	NPD3618	Phase 1
0.8046	Intermediate Similarity	NPD4223	Phase 3
0.8046	Intermediate Similarity	NPD3667	Approved
0.8046	Intermediate Similarity	NPD4221	Approved
0.8043	Intermediate Similarity	NPD6079	Approved
0.8	Intermediate Similarity	NPD3617	Approved
0.7978	Intermediate Similarity	NPD5329	Approved
0.7957	Intermediate Similarity	NPD4202	Approved
0.7931	Intermediate Similarity	NPD4692	Approved
0.7931	Intermediate Similarity	NPD4139	Approved
0.7889	Intermediate Similarity	NPD4694	Approved
0.7889	Intermediate Similarity	NPD5280	Approved
0.7889	Intermediate Similarity	NPD5690	Phase 2
0.7865	Intermediate Similarity	NPD4197	Approved
0.7812	Intermediate Similarity	NPD6084	Phase 2
0.7812	Intermediate Similarity	NPD6083	Phase 2
0.7812	Intermediate Similarity	NPD4755	Approved
0.7789	Intermediate Similarity	NPD5695	Phase 3
0.7753	Intermediate Similarity	NPD4788	Approved
0.7732	Intermediate Similarity	NPD5696	Approved
0.7708	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5221	Approved
0.7708	Intermediate Similarity	NPD5222	Approved
0.7708	Intermediate Similarity	NPD4697	Phase 3
0.7692	Intermediate Similarity	NPD4693	Phase 3
0.7692	Intermediate Similarity	NPD4138	Approved
0.7692	Intermediate Similarity	NPD5205	Approved
0.7692	Intermediate Similarity	NPD4690	Approved
0.7692	Intermediate Similarity	NPD4689	Approved
0.7692	Intermediate Similarity	NPD4688	Approved
0.7692	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5281	Approved
0.766	Intermediate Similarity	NPD5284	Approved
0.7653	Intermediate Similarity	NPD5285	Approved
0.7653	Intermediate Similarity	NPD4700	Approved
0.7653	Intermediate Similarity	NPD5286	Approved
0.7653	Intermediate Similarity	NPD4696	Approved
0.7629	Intermediate Similarity	NPD5173	Approved
0.7579	Intermediate Similarity	NPD6399	Phase 3
0.7576	Intermediate Similarity	NPD5223	Approved
0.7527	Intermediate Similarity	NPD6672	Approved
0.7527	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD5330	Approved
0.7474	Intermediate Similarity	NPD7515	Phase 2
0.7473	Intermediate Similarity	NPD3668	Phase 3
0.7451	Intermediate Similarity	NPD6675	Approved
0.7451	Intermediate Similarity	NPD7128	Approved
0.7451	Intermediate Similarity	NPD6402	Approved
0.7451	Intermediate Similarity	NPD5739	Approved
0.7426	Intermediate Similarity	NPD5174	Approved
0.7426	Intermediate Similarity	NPD5175	Approved
0.7426	Intermediate Similarity	NPD4754	Approved
0.7396	Intermediate Similarity	NPD5133	Approved
0.7379	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD4096	Approved
0.7353	Intermediate Similarity	NPD5141	Approved
0.734	Intermediate Similarity	NPD6903	Approved
0.734	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4634	Approved
0.7326	Intermediate Similarity	NPD5733	Approved
0.7308	Intermediate Similarity	NPD6881	Approved
0.7308	Intermediate Similarity	NPD7320	Approved
0.7308	Intermediate Similarity	NPD6899	Approved
0.7303	Intermediate Similarity	NPD4195	Approved
0.7294	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6050	Approved
0.7282	Intermediate Similarity	NPD4768	Approved
0.7282	Intermediate Similarity	NPD4767	Approved
0.7263	Intermediate Similarity	NPD6080	Approved
0.7263	Intermediate Similarity	NPD6904	Approved
0.7263	Intermediate Similarity	NPD6673	Approved
0.7241	Intermediate Similarity	NPD7339	Approved
0.7241	Intermediate Similarity	NPD6942	Approved
0.7238	Intermediate Similarity	NPD6373	Approved
0.7238	Intermediate Similarity	NPD6372	Approved
0.7222	Intermediate Similarity	NPD7525	Registered
0.7222	Intermediate Similarity	NPD4748	Discontinued
0.7222	Intermediate Similarity	NPD4695	Discontinued
0.7212	Intermediate Similarity	NPD5697	Approved
0.7212	Intermediate Similarity	NPD5701	Approved
0.7204	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD8297	Approved
0.7195	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5692	Phase 3
0.7176	Intermediate Similarity	NPD4244	Approved
0.7176	Intermediate Similarity	NPD4747	Approved
0.7176	Intermediate Similarity	NPD4245	Approved
0.7176	Intermediate Similarity	NPD4789	Approved
0.717	Intermediate Similarity	NPD6883	Approved
0.717	Intermediate Similarity	NPD7102	Approved
0.717	Intermediate Similarity	NPD7290	Approved
0.7159	Intermediate Similarity	NPD6933	Approved
0.7158	Intermediate Similarity	NPD4518	Approved
0.7157	Intermediate Similarity	NPD5091	Approved
0.7143	Intermediate Similarity	NPD5128	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD4730	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD4729	Approved
0.713	Intermediate Similarity	NPD4632	Approved
0.7128	Intermediate Similarity	NPD4623	Approved
0.7128	Intermediate Similarity	NPD4519	Discontinued
0.7126	Intermediate Similarity	NPD4687	Approved
0.7113	Intermediate Similarity	NPD5694	Approved
0.7103	Intermediate Similarity	NPD8130	Phase 1
0.7103	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6869	Approved
0.7103	Intermediate Similarity	NPD6617	Approved
0.7103	Intermediate Similarity	NPD6649	Approved
0.7103	Intermediate Similarity	NPD6847	Approved
0.7103	Intermediate Similarity	NPD6650	Approved
0.7093	Intermediate Similarity	NPD6081	Approved
0.7093	Intermediate Similarity	NPD5276	Approved
0.7091	Intermediate Similarity	NPD7115	Discovery
0.7083	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD6013	Approved
0.7075	Intermediate Similarity	NPD6014	Approved
0.7071	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3698	Phase 2
0.7059	Intermediate Similarity	NPD4137	Phase 3
0.7037	Intermediate Similarity	NPD6882	Approved
0.701	Intermediate Similarity	NPD5207	Approved
0.7009	Intermediate Similarity	NPD5248	Approved
0.7009	Intermediate Similarity	NPD5249	Phase 3
0.7009	Intermediate Similarity	NPD5247	Approved
0.7009	Intermediate Similarity	NPD5135	Approved
0.7009	Intermediate Similarity	NPD5169	Approved
0.7009	Intermediate Similarity	NPD5251	Approved
0.7009	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5250	Approved
0.7	Intermediate Similarity	NPD7614	Phase 1
0.6988	Remote Similarity	NPD7341	Phase 2
0.6981	Remote Similarity	NPD5168	Approved
0.6979	Remote Similarity	NPD5208	Approved
0.6977	Remote Similarity	NPD4691	Approved
0.6966	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6117	Approved
0.6947	Remote Similarity	NPD6098	Approved
0.6944	Remote Similarity	NPD5216	Approved
0.6944	Remote Similarity	NPD5127	Approved
0.6944	Remote Similarity	NPD5215	Approved
0.6944	Remote Similarity	NPD5217	Approved
0.6941	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5360	Phase 3
0.6939	Remote Similarity	NPD5693	Phase 1
0.6932	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6926	Approved
0.6932	Remote Similarity	NPD6924	Approved
0.6931	Remote Similarity	NPD7902	Approved
0.69	Remote Similarity	NPD5654	Approved
0.6897	Remote Similarity	NPD4243	Approved
0.6889	Remote Similarity	NPD6116	Phase 1
0.6863	Remote Similarity	NPD7638	Approved
0.6814	Remote Similarity	NPD4522	Approved
0.6813	Remote Similarity	NPD6118	Approved
0.6813	Remote Similarity	NPD6114	Approved
0.6813	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6115	Approved
0.6813	Remote Similarity	NPD6697	Approved
0.6796	Remote Similarity	NPD7640	Approved
0.6796	Remote Similarity	NPD7639	Approved
0.6786	Remote Similarity	NPD6009	Approved
0.6768	Remote Similarity	NPD8034	Phase 2
0.6768	Remote Similarity	NPD8035	Phase 2
0.6765	Remote Similarity	NPD5959	Approved
0.6759	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5167	Approved
0.6754	Remote Similarity	NPD6059	Approved
0.6754	Remote Similarity	NPD6319	Approved
0.6754	Remote Similarity	NPD6054	Approved
0.6742	Remote Similarity	NPD4058	Approved
0.6742	Remote Similarity	NPD4784	Approved
0.6742	Remote Similarity	NPD4785	Approved
0.6726	Remote Similarity	NPD6335	Approved
0.6696	Remote Similarity	NPD6274	Approved
0.6696	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD7100	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