NPASS Compound

Structure

CID51681 OpenBabel06191715392D 28 30 0 0 1 0 0 0 0 0999 V2000 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 -2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -2.2226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 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 1 7 2 0 0 0 0 2 14 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 6 0 0 0 16 17 1 0 0 0 0 17 23 2 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 15 1 1 0 0 0 20 28 1 0 0 0 0 21 22 1 1 0 0 0 21 26 1 0 0 0 0 22 27 1 1 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.21
Volume:	523.798
LogP:	4.119
LogD:	3.346
LogS:	-3.594
# Rotatable Bonds:	3
TPSA:	145.76
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	6.575
Fsp3:	0.56
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:	-5.068
MDCK Permeability:	2.3371505449176766e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.263
30% Bioavailability (F30%):	0.761

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	96.79578399658203%
Volume Distribution (VD):	1.901
Pgp-substrate:	4.590051174163818%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.141
CYP2C19-inhibitor:	0.426
CYP2C19-substrate:	0.195
CYP2C9-inhibitor:	0.274
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.883

ADMET: Excretion

Clearance (CL):	1.988
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.996
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.009
Carcinogencity:	0.052
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC51681

Natural Product ID:	NPC51681
*Common Name:**	Piperenone
IUPAC Name:	(2S,3R,3aS,7aR)-2-(3,4-dimethoxyphenyl)-3a,7a-dimethoxy-3-methyl-5-prop-2-enyl-3,7-dihydro-2H-1-benzofuran-6-one
Synonyms:
Standard InCHIKey:	IYGFCSHMPLAHTK-WBBCYVCWSA-N
Standard InCHI:	InChI=1S/C22H28O6/c1-7-8-16-12-21(26-5)14(2)20(28-22(21,27-6)13-17(16)23)15-9-10-18(24-3)19(11-15)25-4/h7,9-12,14,20H,1,8,13H2,2-6H3/t14-,20+,21+,22-/m1/s1
SMILES:	C=CCC1=C[C@@]2([C@H](C)[C@@H](c3ccc(c(c3)OC)OC)O[C@@]2(CC1=O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL33562
PubChem CID:	36406703
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

*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
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11040054]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724856]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19900811]
NPO9925	Rhododendron latoucheae	Species	Ericaceae	Eukaryota	Twigs; Leaves	n.a.	n.a.	PMID[30106288]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[8237383]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8368081]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9480	Huperzia miyoshiana	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9480	Huperzia miyoshiana	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1155	Forsythia japonica	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5700	Mortonia hidalgensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6475	Gymnosporia trigyna	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7522	Streptomyces amakusaensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO313	Castilleja sulphurea	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9571	Pseudobrickellia brasiliensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9301	Dioscorea sativa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6666	Eremanthus incanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9925	Rhododendron latoucheae	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19174	Anoplophora chinensis	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2894	Mycena viridimarginata	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9480	Huperzia miyoshiana	Species	Lycopodiaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1372	Individual Protein	Platelet activating factor receptor	Cavia porcellus	Inhibition	=	25.0	%	PMID[474619]

☑ 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 NPC51681 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	388
0.1-0.2	1315
0.2-0.3	2849
0.3-0.4	7009
0.4-0.5	11103
0.5-0.6	5242
0.6-0.7	10285
0.7-0.8	4255
0.8-0.85	210
0.85-0.9	33
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9779	High Similarity	NPC15743
0.9338	High Similarity	NPC166184
0.9248	High Similarity	NPC339621
0.9248	High Similarity	NPC233961
0.9248	High Similarity	NPC280399
0.9021	High Similarity	NPC24257
0.9021	High Similarity	NPC153620
0.8978	High Similarity	NPC145769
0.8978	High Similarity	NPC37065
0.8966	High Similarity	NPC12854
0.8912	High Similarity	NPC308555
0.8889	High Similarity	NPC25496
0.8881	High Similarity	NPC64948
0.8819	High Similarity	NPC30890
0.8803	High Similarity	NPC46180
0.8794	High Similarity	NPC278076
0.8792	High Similarity	NPC254163
0.8786	High Similarity	NPC14022
0.8725	High Similarity	NPC476364
0.8707	High Similarity	NPC475170
0.8618	High Similarity	NPC76211
0.8611	High Similarity	NPC474966
0.8582	High Similarity	NPC209229
0.8562	High Similarity	NPC476337
0.8552	High Similarity	NPC475000
0.8552	High Similarity	NPC474036
0.8552	High Similarity	NPC50696
0.8542	High Similarity	NPC210354
0.8542	High Similarity	NPC104956
0.8542	High Similarity	NPC176586
0.8523	High Similarity	NPC62354
0.8514	High Similarity	NPC472567
0.8511	High Similarity	NPC211386
0.8507	High Similarity	NPC256167
0.8503	High Similarity	NPC476336
0.8503	High Similarity	NPC476338
0.8503	High Similarity	NPC476359
0.85	High Similarity	NPC205915
0.85	High Similarity	NPC327410
0.8493	Intermediate Similarity	NPC474158
0.8493	Intermediate Similarity	NPC223185
0.8467	Intermediate Similarity	NPC223807
0.8467	Intermediate Similarity	NPC151425
0.8467	Intermediate Similarity	NPC56184
0.8451	Intermediate Similarity	NPC102260
0.8451	Intermediate Similarity	NPC230968
0.8446	Intermediate Similarity	NPC473428
0.8442	Intermediate Similarity	NPC218471
0.8442	Intermediate Similarity	NPC239818
0.8435	Intermediate Similarity	NPC472560
0.8435	Intermediate Similarity	NPC3982
0.8435	Intermediate Similarity	NPC193779
0.8435	Intermediate Similarity	NPC213482
0.8425	Intermediate Similarity	NPC191158
0.8425	Intermediate Similarity	NPC177644
0.8421	Intermediate Similarity	NPC476363
0.8417	Intermediate Similarity	NPC477694
0.8417	Intermediate Similarity	NPC477705
0.8414	Intermediate Similarity	NPC40237
0.8414	Intermediate Similarity	NPC151423
0.8411	Intermediate Similarity	NPC327225
0.8408	Intermediate Similarity	NPC476277
0.8406	Intermediate Similarity	NPC57119
0.8406	Intermediate Similarity	NPC158471
0.8406	Intermediate Similarity	NPC165128
0.8406	Intermediate Similarity	NPC226862
0.8403	Intermediate Similarity	NPC147379
0.8403	Intermediate Similarity	NPC322021
0.8403	Intermediate Similarity	NPC470855
0.84	Intermediate Similarity	NPC163002
0.8389	Intermediate Similarity	NPC477698
0.838	Intermediate Similarity	NPC174191
0.838	Intermediate Similarity	NPC44245
0.838	Intermediate Similarity	NPC72796
0.8357	Intermediate Similarity	NPC477706
0.8357	Intermediate Similarity	NPC82111
0.8357	Intermediate Similarity	NPC227160
0.8357	Intermediate Similarity	NPC469480
0.8356	Intermediate Similarity	NPC474288
0.8356	Intermediate Similarity	NPC472564
0.8355	Intermediate Similarity	NPC348849
0.8355	Intermediate Similarity	NPC25127
0.8355	Intermediate Similarity	NPC478213
0.8355	Intermediate Similarity	NPC178195
0.8345	Intermediate Similarity	NPC100675
0.8344	Intermediate Similarity	NPC476335
0.8333	Intermediate Similarity	NPC229882
0.8333	Intermediate Similarity	NPC177830
0.8333	Intermediate Similarity	NPC478199
0.8333	Intermediate Similarity	NPC158635
0.8333	Intermediate Similarity	NPC233780
0.8322	Intermediate Similarity	NPC40654
0.8322	Intermediate Similarity	NPC262804
0.8321	Intermediate Similarity	NPC85830
0.8312	Intermediate Similarity	NPC475663
0.8312	Intermediate Similarity	NPC258644
0.8312	Intermediate Similarity	NPC286919
0.8311	Intermediate Similarity	NPC224687
0.8311	Intermediate Similarity	NPC296575
0.831	Intermediate Similarity	NPC110958
0.831	Intermediate Similarity	NPC19890
0.8301	Intermediate Similarity	NPC186316
0.8299	Intermediate Similarity	NPC218841
0.8299	Intermediate Similarity	NPC92693
0.8298	Intermediate Similarity	NPC7744
0.8296	Intermediate Similarity	NPC65933
0.8296	Intermediate Similarity	NPC172676
0.8296	Intermediate Similarity	NPC57268
0.8296	Intermediate Similarity	NPC216929
0.8296	Intermediate Similarity	NPC312713
0.8296	Intermediate Similarity	NPC126935
0.8289	Intermediate Similarity	NPC68882
0.8289	Intermediate Similarity	NPC153008
0.8289	Intermediate Similarity	NPC148497
0.8288	Intermediate Similarity	NPC253481
0.8288	Intermediate Similarity	NPC253722
0.8288	Intermediate Similarity	NPC31751
0.8286	Intermediate Similarity	NPC142985
0.8286	Intermediate Similarity	NPC233224
0.8286	Intermediate Similarity	NPC271208
0.8278	Intermediate Similarity	NPC164082
0.8269	Intermediate Similarity	NPC34376
0.8267	Intermediate Similarity	NPC478242
0.8258	Intermediate Similarity	NPC469384
0.8258	Intermediate Similarity	NPC325122
0.8255	Intermediate Similarity	NPC221383
0.8255	Intermediate Similarity	NPC299090
0.8255	Intermediate Similarity	NPC143892
0.8255	Intermediate Similarity	NPC30720
0.8255	Intermediate Similarity	NPC283081
0.8252	Intermediate Similarity	NPC470990
0.8248	Intermediate Similarity	NPC18449
0.8248	Intermediate Similarity	NPC34902
0.8248	Intermediate Similarity	NPC121783
0.8247	Intermediate Similarity	NPC478055
0.8247	Intermediate Similarity	NPC155063
0.8247	Intermediate Similarity	NPC477380
0.8247	Intermediate Similarity	NPC301897
0.8243	Intermediate Similarity	NPC327052
0.8239	Intermediate Similarity	NPC1474
0.8239	Intermediate Similarity	NPC42230
0.8239	Intermediate Similarity	NPC136750
0.8239	Intermediate Similarity	NPC474948
0.8239	Intermediate Similarity	NPC266848
0.8235	Intermediate Similarity	NPC57211
0.8235	Intermediate Similarity	NPC287504
0.8235	Intermediate Similarity	NPC136757
0.8231	Intermediate Similarity	NPC86455
0.8231	Intermediate Similarity	NPC137920
0.8231	Intermediate Similarity	NPC125134
0.8228	Intermediate Similarity	NPC474301
0.8228	Intermediate Similarity	NPC475738
0.8228	Intermediate Similarity	NPC180586
0.8224	Intermediate Similarity	NPC220577
0.8224	Intermediate Similarity	NPC279061
0.8224	Intermediate Similarity	NPC476434
0.8224	Intermediate Similarity	NPC477699
0.8219	Intermediate Similarity	NPC28398
0.8212	Intermediate Similarity	NPC227980
0.8207	Intermediate Similarity	NPC178290
0.8201	Intermediate Similarity	NPC286683
0.82	Intermediate Similarity	NPC1580
0.8194	Intermediate Similarity	NPC220462
0.8194	Intermediate Similarity	NPC477885
0.8194	Intermediate Similarity	NPC310206
0.8194	Intermediate Similarity	NPC476340
0.8194	Intermediate Similarity	NPC160425
0.8194	Intermediate Similarity	NPC40920
0.8194	Intermediate Similarity	NPC90431
0.8194	Intermediate Similarity	NPC223335
0.8194	Intermediate Similarity	NPC143895
0.8188	Intermediate Similarity	NPC476362
0.8182	Intermediate Similarity	NPC267242
0.8182	Intermediate Similarity	NPC478238
0.8182	Intermediate Similarity	NPC38699
0.8182	Intermediate Similarity	NPC188962
0.8182	Intermediate Similarity	NPC311339
0.8182	Intermediate Similarity	NPC202249
0.8182	Intermediate Similarity	NPC42871
0.8176	Intermediate Similarity	NPC27159
0.8176	Intermediate Similarity	NPC239608
0.8176	Intermediate Similarity	NPC46161
0.8176	Intermediate Similarity	NPC304956
0.8176	Intermediate Similarity	NPC46880
0.8175	Intermediate Similarity	NPC244876
0.817	Intermediate Similarity	NPC299706
0.817	Intermediate Similarity	NPC115466
0.817	Intermediate Similarity	NPC52623
0.817	Intermediate Similarity	NPC245615
0.817	Intermediate Similarity	NPC44730
0.817	Intermediate Similarity	NPC61604
0.8169	Intermediate Similarity	NPC171928
0.8169	Intermediate Similarity	NPC65183
0.8169	Intermediate Similarity	NPC16830
0.8169	Intermediate Similarity	NPC100223
0.8169	Intermediate Similarity	NPC158526
0.8169	Intermediate Similarity	NPC33611
0.8169	Intermediate Similarity	NPC261812
0.8169	Intermediate Similarity	NPC72046
0.8169	Intermediate Similarity	NPC129687

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 NPC51681 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	824
0.2-0.3	1686
0.3-0.4	2621
0.4-0.5	2030
0.5-0.6	1102
0.6-0.7	499
0.7-0.8	68
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
0.8162	Intermediate Similarity	NPD3705	Approved
0.8089	Intermediate Similarity	NPD5494	Approved
0.8079	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD37	Approved
0.7901	Intermediate Similarity	NPD3818	Discontinued
0.7898	Intermediate Similarity	NPD4966	Approved
0.7898	Intermediate Similarity	NPD4967	Phase 2
0.7898	Intermediate Similarity	NPD4965	Approved
0.7806	Intermediate Similarity	NPD7028	Phase 2
0.7799	Intermediate Similarity	NPD6234	Discontinued
0.7794	Intermediate Similarity	NPD5536	Phase 2
0.7738	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3882	Suspended
0.763	Intermediate Similarity	NPD5283	Phase 1
0.7595	Intermediate Similarity	NPD1934	Approved
0.7566	Intermediate Similarity	NPD4110	Phase 3
0.7566	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD1247	Approved
0.747	Intermediate Similarity	NPD7228	Approved
0.7469	Intermediate Similarity	NPD919	Approved
0.7438	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2801	Approved
0.7425	Intermediate Similarity	NPD7054	Approved
0.7421	Intermediate Similarity	NPD6386	Approved
0.7421	Intermediate Similarity	NPD6385	Approved
0.7417	Intermediate Similarity	NPD2796	Approved
0.7413	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5353	Approved
0.7383	Intermediate Similarity	NPD447	Suspended
0.7381	Intermediate Similarity	NPD7472	Approved
0.7379	Intermediate Similarity	NPD2798	Approved
0.7378	Intermediate Similarity	NPD8127	Discontinued
0.7365	Intermediate Similarity	NPD3751	Discontinued
0.7347	Intermediate Similarity	NPD3027	Phase 3
0.7338	Intermediate Similarity	NPD4628	Phase 3
0.7305	Intermediate Similarity	NPD7473	Discontinued
0.7305	Intermediate Similarity	NPD1357	Approved
0.7303	Intermediate Similarity	NPD2438	Suspended
0.7301	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7240	Approved
0.7294	Intermediate Similarity	NPD6559	Discontinued
0.729	Intermediate Similarity	NPD6190	Approved
0.7289	Intermediate Similarity	NPD5242	Approved
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7255	Intermediate Similarity	NPD7266	Discontinued
0.7255	Intermediate Similarity	NPD1375	Discontinued
0.7254	Intermediate Similarity	NPD17	Approved
0.7251	Intermediate Similarity	NPD7808	Phase 3
0.7251	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6166	Phase 2
0.7246	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1876	Approved
0.7239	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2799	Discontinued
0.7235	Intermediate Similarity	NPD6797	Phase 2
0.7229	Intermediate Similarity	NPD6232	Discontinued
0.7229	Intermediate Similarity	NPD3787	Discontinued
0.7226	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD9494	Approved
0.72	Intermediate Similarity	NPD2979	Phase 3
0.7197	Intermediate Similarity	NPD6799	Approved
0.7193	Intermediate Similarity	NPD7251	Discontinued
0.719	Intermediate Similarity	NPD2935	Discontinued
0.7185	Intermediate Similarity	NPD1358	Approved
0.7183	Intermediate Similarity	NPD1651	Approved
0.717	Intermediate Similarity	NPD920	Approved
0.7152	Intermediate Similarity	NPD230	Phase 1
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7152	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD5647	Approved
0.7125	Intermediate Similarity	NPD1653	Approved
0.7124	Intermediate Similarity	NPD3748	Approved
0.7119	Intermediate Similarity	NPD7296	Approved
0.7118	Intermediate Similarity	NPD5844	Phase 1
0.7117	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7819	Suspended
0.7115	Intermediate Similarity	NPD8166	Discontinued
0.7115	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4420	Approved
0.7111	Intermediate Similarity	NPD3134	Approved
0.7103	Intermediate Similarity	NPD1608	Approved
0.7103	Intermediate Similarity	NPD3972	Approved
0.7097	Intermediate Similarity	NPD2424	Discontinued
0.7097	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1511	Approved
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7086	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5402	Approved
0.7067	Intermediate Similarity	NPD3764	Approved
0.7063	Intermediate Similarity	NPD5691	Approved
0.7063	Intermediate Similarity	NPD5585	Approved
0.7059	Intermediate Similarity	NPD7097	Phase 1
0.7051	Intermediate Similarity	NPD6674	Discontinued
0.7047	Intermediate Similarity	NPD6832	Phase 2
0.7044	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3146	Approved
0.7041	Intermediate Similarity	NPD2403	Approved
0.7039	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1281	Approved
0.7032	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6002	Phase 3
0.7032	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6004	Phase 3
0.7032	Intermediate Similarity	NPD6005	Phase 3
0.702	Intermediate Similarity	NPD8032	Phase 2
0.702	Intermediate Similarity	NPD6233	Phase 2
0.7019	Intermediate Similarity	NPD4210	Discontinued
0.7013	Intermediate Similarity	NPD1510	Phase 2
0.7013	Intermediate Similarity	NPD7033	Discontinued
0.7011	Intermediate Similarity	NPD8313	Approved
0.7011	Intermediate Similarity	NPD8312	Approved
0.7	Intermediate Similarity	NPD1512	Approved
0.6994	Remote Similarity	NPD6873	Phase 2
0.6993	Remote Similarity	NPD6653	Approved
0.6993	Remote Similarity	NPD2492	Phase 1
0.6988	Remote Similarity	NPD7075	Discontinued
0.6987	Remote Similarity	NPD1549	Phase 2
0.6986	Remote Similarity	NPD2981	Phase 2
0.6981	Remote Similarity	NPD4357	Discontinued
0.6975	Remote Similarity	NPD7458	Discontinued
0.6974	Remote Similarity	NPD1240	Approved
0.6971	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5978	Approved
0.697	Remote Similarity	NPD5977	Approved
0.6962	Remote Similarity	NPD3887	Approved
0.6959	Remote Similarity	NPD3266	Approved
0.6959	Remote Similarity	NPD3267	Approved
0.6957	Remote Similarity	NPD5006	Approved
0.6957	Remote Similarity	NPD5005	Approved
0.6954	Remote Similarity	NPD6798	Discontinued
0.6954	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6801	Discontinued
0.6943	Remote Similarity	NPD2800	Approved
0.6943	Remote Similarity	NPD1243	Approved
0.6943	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2983	Phase 2
0.6939	Remote Similarity	NPD2982	Phase 2
0.6937	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD2344	Approved
0.6923	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5058	Phase 3
0.6918	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8455	Phase 2
0.6899	Remote Similarity	NPD3750	Approved
0.6894	Remote Similarity	NPD6273	Approved
0.6892	Remote Similarity	NPD1283	Approved
0.6887	Remote Similarity	NPD7095	Approved
0.6883	Remote Similarity	NPD1607	Approved
0.6871	Remote Similarity	NPD3226	Approved
0.6867	Remote Similarity	NPD3018	Phase 2
0.6867	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2861	Phase 2
0.6863	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1613	Approved
0.6859	Remote Similarity	NPD2531	Phase 2
0.6857	Remote Similarity	NPD228	Approved
0.6855	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5403	Approved
0.6846	Remote Similarity	NPD2797	Approved
0.6845	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3268	Approved
0.6842	Remote Similarity	NPD2313	Discontinued
0.6839	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4236	Phase 3
0.6835	Remote Similarity	NPD4237	Approved
0.6835	Remote Similarity	NPD2067	Discontinued
0.6832	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5401	Approved
0.6826	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4359	Approved
0.6818	Remote Similarity	NPD3657	Discovery
0.6816	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1471	Phase 3
0.6813	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1465	Phase 2
0.6807	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1091	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