NPASS Compound

Structure

CID47834 OpenBabel06191715382D 32 34 0 0 1 0 0 0 0 0999 V2000 4.6103 2.7545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4287 -0.1666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6650 1.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2885 3.9494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2359 3.3093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2595 1.4341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2624 1.6148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7171 0.5728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5518 1.0555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7337 -1.2636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9146 0.4752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7171 -0.1098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4119 -1.4019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0691 0.5728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6074 2.5738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8542 -0.2207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2345 1.0555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3397 -0.2818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9494 3.3520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6704 2.1080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1141 0.5551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9501 0.8042 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2345 -0.5925 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 0.6139 -0.7453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2944 4.3109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9769 3.0119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9812 1.0905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9465 3.1712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7999 2.2567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5202 0.2497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1420 1.1768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 7 1 0 0 0 0 6 11 2 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 17 2 0 0 0 0 9 14 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 19 1 0 0 0 0 16 25 2 0 0 0 0 16 31 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 6 0 0 0 18 24 1 0 0 0 0 19 26 2 0 0 0 0 19 29 1 0 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 21 28 2 0 0 0 0 21 32 1 0 0 0 0 22 3 1 1 0 0 0 22 32 1 0 0 0 0 23 24 1 1 0 0 0 24 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.19
Volume:	449.857
LogP:	1.829
LogD:	1.2
LogS:	-4.539
# Rotatable Bonds:	8
TPSA:	105.2
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	5.654
Fsp3:	0.583
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:	-4.95
MDCK Permeability:	4.5084074372425675e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.874
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.876
Plasma Protein Binding (PPB):	28.310115814208984%
Volume Distribution (VD):	0.701
Pgp-substrate:	46.561012268066406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.938
CYP2C19-inhibitor:	0.885
CYP2C19-substrate:	0.791
CYP2C9-inhibitor:	0.234
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.178
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.946
CYP3A4-substrate:	0.759

ADMET: Excretion

Clearance (CL):	4.519
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.4
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.542
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.086
Carcinogencity:	0.617
Eye Corrosion:	0.01
Eye Irritation:	0.069
Respiratory Toxicity:	0.32

Download Data

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

Natural Product: NPC47834

Natural Product ID:	NPC47834
*Common Name:**	DXNRJQIZAXOHQJ-KYNXZXPVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DXNRJQIZAXOHQJ-KYNXZXPVSA-N
Standard InCHI:	InChI=1S/C24H30O8/c1-15(19(26)29-4)7-6-11-22(3)18-10-13-23(21(28)32-22)12-8-17(20(27)30-5)9-14-24(18,23)31-16(2)25/h6-8,11,18H,9-10,12-14H2,1-5H3/b11-6+,15-7+/t18-,22+,23+,24-/m0/s1
SMILES:	C/C(=CC=C[C@]1(C)[C@@H]2CC[C@]3(CC=C(CC[C@]23OC(=O)C)C(=O)OC)C(=O)O1)/C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513582
PubChem CID:	6475944
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346966]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root bark	n.a.	n.a.	PMID[14527554]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	tuber	n.a.	PMID[15180301]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	leaves,?stems	USA	n.a.	PMID[16124770]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17291040]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17381154]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	root and trunk bark	n.a.	n.a.	PMID[18078313]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078313]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23668986]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25843525]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760078]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377017]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29968	Pseudolarix kaempferi	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21914	Turnera angustifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO385	Bipolaris oryzae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20328	Plumeria acutifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22700	Dacrydium comosum	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22309	Gastrodia elata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21090	Chrysanthemum ornatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16955	Pseudolarix amabilis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20772	Pedalium murex	Species	Pedaliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5178	Pelophylax nigromaculatus	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20262	Delia paludosa	Species	Anthomyiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20140	Aloe perryi	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22563	Sclerocarya birrea	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22239	Hibiscus vitifolius	Species	Malvaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IZ	=	1.0	mm	PMID[570519]
NPT20	Organism	Candida albicans	Candida albicans	IZ	<	1.0	mm	PMID[570519]

☑ 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 NPC47834 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	225
0.1-0.2	1139
0.2-0.3	4656
0.3-0.4	9132
0.4-0.5	14201
0.5-0.6	7760
0.6-0.7	4967
0.7-0.8	599
0.8-0.85	6
0.85-0.9	3
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9574	High Similarity	NPC66110
0.9468	High Similarity	NPC62670
0.9468	High Similarity	NPC116139
0.9255	High Similarity	NPC244411
0.9158	High Similarity	NPC280963
0.9043	High Similarity	NPC9812
0.8854	High Similarity	NPC64742
0.8673	High Similarity	NPC206079
0.86	High Similarity	NPC309190
0.8333	Intermediate Similarity	NPC13710
0.8229	Intermediate Similarity	NPC472705
0.8119	Intermediate Similarity	NPC475099
0.8108	Intermediate Similarity	NPC470829
0.8108	Intermediate Similarity	NPC473228
0.8041	Intermediate Similarity	NPC221282
0.8041	Intermediate Similarity	NPC290651
0.7921	Intermediate Similarity	NPC470188
0.7905	Intermediate Similarity	NPC476958
0.7905	Intermediate Similarity	NPC470192
0.7826	Intermediate Similarity	NPC47747
0.7822	Intermediate Similarity	NPC213947
0.7822	Intermediate Similarity	NPC108475
0.7822	Intermediate Similarity	NPC170143
0.7812	Intermediate Similarity	NPC478145
0.7802	Intermediate Similarity	NPC63445
0.7802	Intermediate Similarity	NPC222210
0.7755	Intermediate Similarity	NPC77337
0.7748	Intermediate Similarity	NPC476959
0.7714	Intermediate Similarity	NPC169843
0.7708	Intermediate Similarity	NPC261253
0.7708	Intermediate Similarity	NPC469676
0.7708	Intermediate Similarity	NPC474045
0.7692	Intermediate Similarity	NPC49393
0.7692	Intermediate Similarity	NPC105725
0.7677	Intermediate Similarity	NPC284185
0.7647	Intermediate Similarity	NPC477949
0.7642	Intermediate Similarity	NPC291643
0.7629	Intermediate Similarity	NPC478144
0.7624	Intermediate Similarity	NPC67584
0.7624	Intermediate Similarity	NPC37408
0.7619	Intermediate Similarity	NPC470954
0.7615	Intermediate Similarity	NPC475495
0.7604	Intermediate Similarity	NPC99395
0.7604	Intermediate Similarity	NPC197903
0.7604	Intermediate Similarity	NPC235792
0.76	Intermediate Similarity	NPC476049
0.7596	Intermediate Similarity	NPC477950
0.7596	Intermediate Similarity	NPC171759
0.7596	Intermediate Similarity	NPC298233
0.7579	Intermediate Similarity	NPC170377
0.7576	Intermediate Similarity	NPC253144
0.7549	Intermediate Similarity	NPC118159
0.7549	Intermediate Similarity	NPC213078
0.7545	Intermediate Similarity	NPC123855
0.7545	Intermediate Similarity	NPC477093
0.7545	Intermediate Similarity	NPC473522
0.7545	Intermediate Similarity	NPC475277
0.7545	Intermediate Similarity	NPC76550
0.7544	Intermediate Similarity	NPC476962
0.7525	Intermediate Similarity	NPC476267
0.7525	Intermediate Similarity	NPC90453
0.7524	Intermediate Similarity	NPC471993
0.7524	Intermediate Similarity	NPC475091
0.7523	Intermediate Similarity	NPC477103
0.75	Intermediate Similarity	NPC191339
0.75	Intermediate Similarity	NPC55602
0.75	Intermediate Similarity	NPC45579
0.75	Intermediate Similarity	NPC70595
0.75	Intermediate Similarity	NPC74103
0.75	Intermediate Similarity	NPC286341
0.75	Intermediate Similarity	NPC150978
0.75	Intermediate Similarity	NPC123177
0.75	Intermediate Similarity	NPC476963
0.7477	Intermediate Similarity	NPC46269
0.7477	Intermediate Similarity	NPC470975
0.7477	Intermediate Similarity	NPC103088
0.7477	Intermediate Similarity	NPC470979
0.7477	Intermediate Similarity	NPC106395
0.7476	Intermediate Similarity	NPC202705
0.7476	Intermediate Similarity	NPC40812
0.7476	Intermediate Similarity	NPC2049
0.7476	Intermediate Similarity	NPC161493
0.7453	Intermediate Similarity	NPC110989
0.7451	Intermediate Similarity	NPC474490
0.7451	Intermediate Similarity	NPC272050
0.7451	Intermediate Similarity	NPC469873
0.7451	Intermediate Similarity	NPC52044
0.7447	Intermediate Similarity	NPC474510
0.7434	Intermediate Similarity	NPC239273
0.7431	Intermediate Similarity	NPC477102
0.7429	Intermediate Similarity	NPC474742
0.7429	Intermediate Similarity	NPC146822
0.7426	Intermediate Similarity	NPC308656
0.7426	Intermediate Similarity	NPC473234
0.7426	Intermediate Similarity	NPC473263
0.7426	Intermediate Similarity	NPC60386
0.7426	Intermediate Similarity	NPC473273
0.7423	Intermediate Similarity	NPC476628
0.7423	Intermediate Similarity	NPC474547
0.7411	Intermediate Similarity	NPC138303
0.7411	Intermediate Similarity	NPC67290
0.7411	Intermediate Similarity	NPC470953
0.7411	Intermediate Similarity	NPC133677
0.7404	Intermediate Similarity	NPC308567
0.7404	Intermediate Similarity	NPC471932
0.7404	Intermediate Similarity	NPC255592
0.7404	Intermediate Similarity	NPC261377
0.74	Intermediate Similarity	NPC62815
0.74	Intermediate Similarity	NPC301969
0.74	Intermediate Similarity	NPC37607
0.7396	Intermediate Similarity	NPC318468
0.7391	Intermediate Similarity	NPC147635
0.7391	Intermediate Similarity	NPC163693
0.7387	Intermediate Similarity	NPC313921
0.7387	Intermediate Similarity	NPC138757
0.7387	Intermediate Similarity	NPC98038
0.7383	Intermediate Similarity	NPC100487
0.7383	Intermediate Similarity	NPC470297
0.7383	Intermediate Similarity	NPC471143
0.7383	Intermediate Similarity	NPC203659
0.7383	Intermediate Similarity	NPC477510
0.7383	Intermediate Similarity	NPC239162
0.7379	Intermediate Similarity	NPC58052
0.7379	Intermediate Similarity	NPC111684
0.7379	Intermediate Similarity	NPC126156
0.7374	Intermediate Similarity	NPC471956
0.7368	Intermediate Similarity	NPC470420
0.7368	Intermediate Similarity	NPC288679
0.7368	Intermediate Similarity	NPC473720
0.7364	Intermediate Similarity	NPC41551
0.7364	Intermediate Similarity	NPC50223
0.7358	Intermediate Similarity	NPC471757
0.7358	Intermediate Similarity	NPC478156
0.7358	Intermediate Similarity	NPC78127
0.7358	Intermediate Similarity	NPC225353
0.7358	Intermediate Similarity	NPC475750
0.7353	Intermediate Similarity	NPC166143
0.7353	Intermediate Similarity	NPC471994
0.7353	Intermediate Similarity	NPC127019
0.7353	Intermediate Similarity	NPC281775
0.7353	Intermediate Similarity	NPC140543
0.7353	Intermediate Similarity	NPC477131
0.7353	Intermediate Similarity	NPC120351
0.735	Intermediate Similarity	NPC472768
0.7347	Intermediate Similarity	NPC122502
0.7347	Intermediate Similarity	NPC234038
0.734	Intermediate Similarity	NPC469617
0.734	Intermediate Similarity	NPC469620
0.734	Intermediate Similarity	NPC469690
0.7333	Intermediate Similarity	NPC475053
0.7333	Intermediate Similarity	NPC13743
0.7333	Intermediate Similarity	NPC469864
0.7333	Intermediate Similarity	NPC98813
0.7333	Intermediate Similarity	NPC469872
0.7321	Intermediate Similarity	NPC101965
0.7321	Intermediate Similarity	NPC101400
0.7321	Intermediate Similarity	NPC209058
0.732	Intermediate Similarity	NPC14575
0.732	Intermediate Similarity	NPC196487
0.732	Intermediate Similarity	NPC238197
0.7315	Intermediate Similarity	NPC223450
0.7315	Intermediate Similarity	NPC314244
0.7312	Intermediate Similarity	NPC145898
0.7304	Intermediate Similarity	NPC472667
0.7304	Intermediate Similarity	NPC475520
0.73	Intermediate Similarity	NPC115179
0.73	Intermediate Similarity	NPC166919
0.73	Intermediate Similarity	NPC78008
0.73	Intermediate Similarity	NPC106040
0.73	Intermediate Similarity	NPC212598
0.729	Intermediate Similarity	NPC475945
0.729	Intermediate Similarity	NPC473283
0.729	Intermediate Similarity	NPC475871
0.729	Intermediate Similarity	NPC329345
0.729	Intermediate Similarity	NPC475526
0.7282	Intermediate Similarity	NPC209355
0.7282	Intermediate Similarity	NPC213698
0.7282	Intermediate Similarity	NPC171395
0.7281	Intermediate Similarity	NPC471145
0.7281	Intermediate Similarity	NPC475305
0.7273	Intermediate Similarity	NPC47951
0.7273	Intermediate Similarity	NPC475703
0.7264	Intermediate Similarity	NPC474912
0.7264	Intermediate Similarity	NPC150923
0.7264	Intermediate Similarity	NPC474899
0.7257	Intermediate Similarity	NPC265290
0.7257	Intermediate Similarity	NPC305044
0.7255	Intermediate Similarity	NPC153590
0.7245	Intermediate Similarity	NPC155873
0.7245	Intermediate Similarity	NPC245434
0.7241	Intermediate Similarity	NPC4548
0.7241	Intermediate Similarity	NPC143755
0.7241	Intermediate Similarity	NPC184555
0.7241	Intermediate Similarity	NPC472004
0.7238	Intermediate Similarity	NPC141191
0.7238	Intermediate Similarity	NPC83895
0.7238	Intermediate Similarity	NPC187761
0.7238	Intermediate Similarity	NPC54843
0.7238	Intermediate Similarity	NPC221615
0.7232	Intermediate Similarity	NPC265391

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 NPC47834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1402
0.2-0.3	3869
0.3-0.4	2429
0.4-0.5	812
0.5-0.6	267
0.6-0.7	172
0.7-0.8	5
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
0.7292	Intermediate Similarity	NPD5209	Approved
0.7207	Intermediate Similarity	NPD6371	Approved
0.7115	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5785	Approved
0.699	Remote Similarity	NPD5693	Phase 1
0.699	Remote Similarity	NPD5694	Approved
0.6961	Remote Similarity	NPD1695	Approved
0.693	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD5779	Approved
0.6923	Remote Similarity	NPD5778	Approved
0.6893	Remote Similarity	NPD5207	Approved
0.6893	Remote Similarity	NPD5692	Phase 3
0.6827	Remote Similarity	NPD7637	Suspended
0.6827	Remote Similarity	NPD6050	Approved
0.6827	Remote Similarity	NPD6411	Approved
0.6827	Remote Similarity	NPD7983	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6774	Remote Similarity	NPD7319	Approved
0.6737	Remote Similarity	NPD8039	Approved
0.6733	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD1694	Approved
0.6731	Remote Similarity	NPD6698	Approved
0.6731	Remote Similarity	NPD46	Approved
0.6729	Remote Similarity	NPD7839	Suspended
0.6726	Remote Similarity	NPD6686	Approved
0.6698	Remote Similarity	NPD5282	Discontinued
0.6696	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6637	Remote Similarity	NPD5697	Approved
0.6636	Remote Similarity	NPD5695	Phase 3
0.6635	Remote Similarity	NPD6080	Approved
0.6635	Remote Similarity	NPD6673	Approved
0.6635	Remote Similarity	NPD6904	Approved
0.6635	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6101	Approved
0.6606	Remote Similarity	NPD7638	Approved
0.6602	Remote Similarity	NPD3573	Approved
0.6579	Remote Similarity	NPD6899	Approved
0.6579	Remote Similarity	NPD6881	Approved
0.6571	Remote Similarity	NPD7838	Discovery
0.6569	Remote Similarity	NPD5363	Approved
0.6555	Remote Similarity	NPD7115	Discovery
0.6552	Remote Similarity	NPD6649	Approved
0.6552	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD7639	Approved
0.6545	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD5737	Approved
0.6538	Remote Similarity	NPD5208	Approved
0.6538	Remote Similarity	NPD6672	Approved
0.6522	Remote Similarity	NPD6012	Approved
0.6522	Remote Similarity	NPD6013	Approved
0.6522	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6083	Phase 2
0.6514	Remote Similarity	NPD6084	Phase 2
0.6505	Remote Similarity	NPD7146	Approved
0.6505	Remote Similarity	NPD7334	Approved
0.6505	Remote Similarity	NPD5786	Approved
0.6505	Remote Similarity	NPD5330	Approved
0.6505	Remote Similarity	NPD6684	Approved
0.6505	Remote Similarity	NPD6409	Approved
0.6505	Remote Similarity	NPD7521	Approved
0.6496	Remote Similarity	NPD8297	Approved
0.6496	Remote Similarity	NPD6882	Approved
0.6481	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5654	Approved
0.6475	Remote Similarity	NPD7503	Approved
0.6466	Remote Similarity	NPD6883	Approved
0.6466	Remote Similarity	NPD7290	Approved
0.6466	Remote Similarity	NPD7102	Approved
0.6455	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5696	Approved
0.6452	Remote Similarity	NPD7492	Approved
0.6441	Remote Similarity	NPD4632	Approved
0.6436	Remote Similarity	NPD6435	Approved
0.6435	Remote Similarity	NPD6011	Approved
0.641	Remote Similarity	NPD8130	Phase 1
0.641	Remote Similarity	NPD6869	Approved
0.641	Remote Similarity	NPD6617	Approved
0.641	Remote Similarity	NPD6847	Approved
0.6406	Remote Similarity	NPD7260	Phase 2
0.6404	Remote Similarity	NPD6402	Approved
0.6404	Remote Similarity	NPD7128	Approved
0.6404	Remote Similarity	NPD5739	Approved
0.6404	Remote Similarity	NPD6675	Approved
0.64	Remote Similarity	NPD6616	Approved
0.6393	Remote Similarity	NPD6054	Approved
0.6381	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6903	Approved
0.6379	Remote Similarity	NPD6373	Approved
0.6379	Remote Similarity	NPD6372	Approved
0.6373	Remote Similarity	NPD5362	Discontinued
0.6364	Remote Similarity	NPD5959	Approved
0.6364	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7078	Approved
0.6348	Remote Similarity	NPD5701	Approved
0.6346	Remote Similarity	NPD6098	Approved
0.6341	Remote Similarity	NPD8513	Phase 3
0.6341	Remote Similarity	NPD8515	Approved
0.6341	Remote Similarity	NPD6015	Approved
0.6341	Remote Similarity	NPD8517	Approved
0.6341	Remote Similarity	NPD8516	Approved
0.6341	Remote Similarity	NPD6016	Approved
0.6337	Remote Similarity	NPD5369	Approved
0.6325	Remote Similarity	NPD4634	Approved
0.6321	Remote Similarity	NPD6051	Approved
0.6306	Remote Similarity	NPD4225	Approved
0.6299	Remote Similarity	NPD7736	Approved
0.6293	Remote Similarity	NPD7320	Approved
0.629	Remote Similarity	NPD5988	Approved
0.629	Remote Similarity	NPD6370	Approved
0.6283	Remote Similarity	NPD5211	Phase 2
0.6281	Remote Similarity	NPD6009	Approved
0.6275	Remote Similarity	NPD4270	Approved
0.6275	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD5286	Approved
0.6239	Remote Similarity	NPD6001	Approved
0.6238	Remote Similarity	NPD5368	Approved
0.6226	Remote Similarity	NPD4518	Approved
0.621	Remote Similarity	NPD5983	Phase 2
0.6207	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5690	Phase 2
0.619	Remote Similarity	NPD4249	Approved
0.619	Remote Similarity	NPD4694	Approved
0.619	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5280	Approved
0.6182	Remote Similarity	NPD4629	Approved
0.6182	Remote Similarity	NPD5210	Approved
0.6174	Remote Similarity	NPD5141	Approved
0.6168	Remote Similarity	NPD4753	Phase 2
0.6165	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5225	Approved
0.614	Remote Similarity	NPD4633	Approved
0.614	Remote Similarity	NPD5224	Approved
0.614	Remote Similarity	NPD5226	Approved
0.6132	Remote Similarity	NPD4250	Approved
0.6132	Remote Similarity	NPD4251	Approved
0.6129	Remote Similarity	NPD6059	Approved
0.6117	Remote Similarity	NPD4221	Approved
0.6117	Remote Similarity	NPD4223	Phase 3
0.6111	Remote Similarity	NPD7830	Approved
0.6111	Remote Similarity	NPD7604	Phase 2
0.6111	Remote Similarity	NPD7829	Approved
0.6098	Remote Similarity	NPD7328	Approved
0.6098	Remote Similarity	NPD7327	Approved
0.6095	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD8074	Phase 3
0.6094	Remote Similarity	NPD8293	Discontinued
0.6087	Remote Similarity	NPD5175	Approved
0.6087	Remote Similarity	NPD5174	Approved
0.6078	Remote Similarity	NPD4821	Approved
0.6078	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4822	Approved
0.6078	Remote Similarity	NPD4820	Approved
0.6078	Remote Similarity	NPD4252	Approved
0.6078	Remote Similarity	NPD4819	Approved
0.6071	Remote Similarity	NPD4755	Approved
0.6068	Remote Similarity	NPD6412	Phase 2
0.6068	Remote Similarity	NPD6614	Approved
0.6066	Remote Similarity	NPD6274	Approved
0.6058	Remote Similarity	NPD7154	Phase 3
0.6058	Remote Similarity	NPD6695	Phase 3
0.6055	Remote Similarity	NPD6079	Approved
0.6053	Remote Similarity	NPD5223	Approved
0.605	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7516	Approved
0.6048	Remote Similarity	NPD7101	Approved
0.6048	Remote Similarity	NPD7100	Approved
0.6038	Remote Similarity	NPD5279	Phase 3
0.6017	Remote Similarity	NPD4729	Approved
0.6017	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD4730	Approved
0.6016	Remote Similarity	NPD6317	Approved
0.6016	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD7632	Discontinued
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4197	Approved
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD8377	Approved
0.5985	Remote Similarity	NPD6845	Suspended
0.5982	Remote Similarity	NPD5221	Approved
0.5982	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5222	Approved
0.5968	Remote Similarity	NPD6313	Approved
0.5968	Remote Similarity	NPD6314	Approved
0.5968	Remote Similarity	NPD6335	Approved
0.5966	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4700	Approved
0.5965	Remote Similarity	NPD6404	Discontinued
0.5963	Remote Similarity	NPD4096	Approved
0.596	Remote Similarity	NPD4687	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