NPASS Compound

Structure

NPC46180 OpenBabel07101719252D 31 32 0 0 1 0 0 0 0 0999 V2000 1.1849 -2.3656 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3257 3.2004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0544 -1.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5867 1.2175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7172 0.2261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 -0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6628 1.6002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9239 -0.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0544 -1.3741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5323 2.5917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 3 16 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 30 1 0 0 0 0 8 11 1 0 0 0 0 9 10 2 0 0 0 0 9 18 1 0 0 0 0 10 21 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 13 20 2 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 2 1 6 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 25 2 0 0 0 0 16 31 1 0 0 0 0 17 22 1 0 0 0 0 18 27 1 6 0 0 0 19 23 2 0 0 0 0 19 28 1 0 0 0 0 20 23 1 0 0 0 0 20 29 1 0 0 0 0 21 24 1 0 0 0 0 21 26 2 0 0 0 0 22 31 1 6 0 0 0 23 30 1 0 0 0 0 24 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.21
Volume:	449.624
LogP:	2.714
LogD:	2.739
LogS:	-3.895
# Rotatable Bonds:	11
TPSA:	80.29
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	4.221
Fsp3:	0.5
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:	-4.659
MDCK Permeability:	1.4517216186504811e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.116
30% Bioavailability (F30%):	0.704

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.902
Plasma Protein Binding (PPB):	76.5196762084961%
Volume Distribution (VD):	1.061
Pgp-substrate:	20.1579532623291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.755
CYP2C19-inhibitor:	0.344
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.272
CYP2C9-substrate:	0.659
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.761
CYP3A4-inhibitor:	0.929
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	5.668
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.307
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.172
Skin Sensitization:	0.378
Carcinogencity:	0.411
Eye Corrosion:	0.006
Eye Irritation:	0.089
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC46180

Natural Product ID:	NPC46180
*Common Name:**	Megaphone Acetate
IUPAC Name:	[(1R,2S)-2-[(1R,5R)-5-methoxy-2-oxo-1-prop-2-enylcyclohex-3-en-1-yl]-1-(3,4,5-trimethoxyphenyl)propyl] acetate
Synonyms:	Megaphone Acetate
Standard InCHIKey:	ACAKNZGFODMHDA-GYJSXLPRSA-N
Standard InCHI:	InChI=1S/C24H32O7/c1-8-11-24(14-18(27-4)9-10-21(24)26)15(2)22(31-16(3)25)17-12-19(28-5)23(30-7)20(13-17)29-6/h8-10,12-13,15,18,22H,1,11,14H2,2-7H3/t15-,18+,22-,24-/m1/s1
SMILES:	C=CC[C@@]1(C[C@H](C=CC1=O)OC)[C@H](C)[C@H](c1cc(c(c(c1)OC)OC)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490171
PubChem CID:	21140766
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001097] Benzyloxycarbonyls

*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
NPO14069	Endlicheria dysodantha	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1665173]
NPO14069	Endlicheria dysodantha	Species	Lauraceae	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
ED50	3
Others	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.59	ug ml-1	PMID[499317]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.66	ug ml-1	PMID[499317]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.52	10'-1 ug/ml	PMID[499317]
NPT140	Organism	Artemia	Artemia	LC50	=	253.6	ppm	PMID[499317]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	48.3	%	PMID[499317]

☑ 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 NPC46180 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	381
0.1-0.2	1324
0.2-0.3	3173
0.3-0.4	6954
0.4-0.5	11057
0.5-0.6	4588
0.6-0.7	7710
0.7-0.8	7149
0.8-0.85	330
0.85-0.9	29
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC37065
0.9078	High Similarity	NPC474966
0.9051	High Similarity	NPC145769
0.8986	High Similarity	NPC211386
0.8889	High Similarity	NPC213482
0.8849	High Similarity	NPC72796
0.8849	High Similarity	NPC44245
0.8803	High Similarity	NPC51681
0.8786	High Similarity	NPC209229
0.8776	High Similarity	NPC475170
0.8759	High Similarity	NPC339621
0.8759	High Similarity	NPC233961
0.8759	High Similarity	NPC280399
0.8705	High Similarity	NPC288743
0.8658	High Similarity	NPC476434
0.8621	High Similarity	NPC475000
0.8621	High Similarity	NPC50696
0.8621	High Similarity	NPC15743
0.8611	High Similarity	NPC176586
0.8611	High Similarity	NPC210354
0.8582	High Similarity	NPC288238
0.8571	High Similarity	NPC30720
0.8571	High Similarity	NPC25496
0.8562	High Similarity	NPC474158
0.8562	High Similarity	NPC232883
0.8552	High Similarity	NPC273657
0.8552	High Similarity	NPC106920
0.8531	High Similarity	NPC470962
0.8503	High Similarity	NPC472560
0.8503	High Similarity	NPC193779
0.8493	Intermediate Similarity	NPC177644
0.8493	Intermediate Similarity	NPC469615
0.8493	Intermediate Similarity	NPC191158
0.8489	Intermediate Similarity	NPC79184
0.8489	Intermediate Similarity	NPC299010
0.8489	Intermediate Similarity	NPC307042
0.8483	Intermediate Similarity	NPC151423
0.8483	Intermediate Similarity	NPC40237
0.8478	Intermediate Similarity	NPC210674
0.8467	Intermediate Similarity	NPC127604
0.8467	Intermediate Similarity	NPC62354
0.8462	Intermediate Similarity	NPC166184
0.8456	Intermediate Similarity	NPC472567
0.8435	Intermediate Similarity	NPC469683
0.8431	Intermediate Similarity	NPC477380
0.8425	Intermediate Similarity	NPC28326
0.8425	Intermediate Similarity	NPC477696
0.8425	Intermediate Similarity	NPC470811
0.8425	Intermediate Similarity	NPC474288
0.8425	Intermediate Similarity	NPC477697
0.8421	Intermediate Similarity	NPC178195
0.8421	Intermediate Similarity	NPC348849
0.8414	Intermediate Similarity	NPC470991
0.8411	Intermediate Similarity	NPC151425
0.8411	Intermediate Similarity	NPC246566
0.8411	Intermediate Similarity	NPC95498
0.8406	Intermediate Similarity	NPC223807
0.8403	Intermediate Similarity	NPC307883
0.84	Intermediate Similarity	NPC473091
0.8394	Intermediate Similarity	NPC173608
0.8392	Intermediate Similarity	NPC143895
0.8389	Intermediate Similarity	NPC262804
0.8389	Intermediate Similarity	NPC40654
0.838	Intermediate Similarity	NPC311339
0.8378	Intermediate Similarity	NPC474446
0.8378	Intermediate Similarity	NPC476362
0.8377	Intermediate Similarity	NPC477885
0.8367	Intermediate Similarity	NPC27159
0.8367	Intermediate Similarity	NPC92693
0.8367	Intermediate Similarity	NPC18211
0.8367	Intermediate Similarity	NPC218841
0.8358	Intermediate Similarity	NPC222175
0.8357	Intermediate Similarity	NPC19242
0.8357	Intermediate Similarity	NPC476399
0.8345	Intermediate Similarity	NPC322021
0.8345	Intermediate Similarity	NPC278076
0.8344	Intermediate Similarity	NPC163002
0.8333	Intermediate Similarity	NPC88297
0.8333	Intermediate Similarity	NPC186845
0.8333	Intermediate Similarity	NPC9891
0.8333	Intermediate Similarity	NPC125570
0.8333	Intermediate Similarity	NPC865
0.8333	Intermediate Similarity	NPC112571
0.8333	Intermediate Similarity	NPC285725
0.8333	Intermediate Similarity	NPC50683
0.8323	Intermediate Similarity	NPC325122
0.8322	Intermediate Similarity	NPC153620
0.8322	Intermediate Similarity	NPC24257
0.8322	Intermediate Similarity	NPC295297
0.8312	Intermediate Similarity	NPC474983
0.8311	Intermediate Similarity	NPC184702
0.8311	Intermediate Similarity	NPC476843
0.8311	Intermediate Similarity	NPC27106
0.8311	Intermediate Similarity	NPC476841
0.831	Intermediate Similarity	NPC233018
0.831	Intermediate Similarity	NPC36437
0.831	Intermediate Similarity	NPC241341
0.8302	Intermediate Similarity	NPC474948
0.8302	Intermediate Similarity	NPC42230
0.8301	Intermediate Similarity	NPC186507
0.8301	Intermediate Similarity	NPC25127
0.8289	Intermediate Similarity	NPC476335
0.8289	Intermediate Similarity	NPC473732
0.8289	Intermediate Similarity	NPC56184
0.8289	Intermediate Similarity	NPC228662
0.8289	Intermediate Similarity	NPC75695
0.8288	Intermediate Similarity	NPC100675
0.8286	Intermediate Similarity	NPC153547
0.8278	Intermediate Similarity	NPC12854
0.8278	Intermediate Similarity	NPC316989
0.8278	Intermediate Similarity	NPC146014
0.8278	Intermediate Similarity	NPC474305
0.8273	Intermediate Similarity	NPC194841
0.8267	Intermediate Similarity	NPC474999
0.8267	Intermediate Similarity	NPC470511
0.8267	Intermediate Similarity	NPC477375
0.8267	Intermediate Similarity	NPC102934
0.8267	Intermediate Similarity	NPC252281
0.8267	Intermediate Similarity	NPC252402
0.8267	Intermediate Similarity	NPC327352
0.8267	Intermediate Similarity	NPC198129
0.8261	Intermediate Similarity	NPC27352
0.8258	Intermediate Similarity	NPC268602
0.8255	Intermediate Similarity	NPC30890
0.8252	Intermediate Similarity	NPC155098
0.8252	Intermediate Similarity	NPC471110
0.8252	Intermediate Similarity	NPC309744
0.8247	Intermediate Similarity	NPC222185
0.8247	Intermediate Similarity	NPC117154
0.8243	Intermediate Similarity	NPC143092
0.8243	Intermediate Similarity	NPC16353
0.8243	Intermediate Similarity	NPC251372
0.8239	Intermediate Similarity	NPC319969
0.8239	Intermediate Similarity	NPC137669
0.8235	Intermediate Similarity	NPC477886
0.8235	Intermediate Similarity	NPC475116
0.8235	Intermediate Similarity	NPC308555
0.8235	Intermediate Similarity	NPC473236
0.8235	Intermediate Similarity	NPC146277
0.8235	Intermediate Similarity	NPC19380
0.8224	Intermediate Similarity	NPC210642
0.8224	Intermediate Similarity	NPC303519
0.8224	Intermediate Similarity	NPC32079
0.8224	Intermediate Similarity	NPC477700
0.8224	Intermediate Similarity	NPC13985
0.8219	Intermediate Similarity	NPC147379
0.8217	Intermediate Similarity	NPC319749
0.8214	Intermediate Similarity	NPC222127
0.8214	Intermediate Similarity	NPC82862
0.8212	Intermediate Similarity	NPC477376
0.8212	Intermediate Similarity	NPC474306
0.8212	Intermediate Similarity	NPC322426
0.8212	Intermediate Similarity	NPC146388
0.8212	Intermediate Similarity	NPC216223
0.8212	Intermediate Similarity	NPC474903
0.8212	Intermediate Similarity	NPC474393
0.8212	Intermediate Similarity	NPC475848
0.8212	Intermediate Similarity	NPC477698
0.8212	Intermediate Similarity	NPC145569
0.8212	Intermediate Similarity	NPC474347
0.8212	Intermediate Similarity	NPC477374
0.821	Intermediate Similarity	NPC474568
0.8207	Intermediate Similarity	NPC471069
0.8207	Intermediate Similarity	NPC281780
0.8207	Intermediate Similarity	NPC471068
0.8201	Intermediate Similarity	NPC154275
0.82	Intermediate Similarity	NPC195919
0.82	Intermediate Similarity	NPC120924
0.82	Intermediate Similarity	NPC216314
0.82	Intermediate Similarity	NPC80230
0.82	Intermediate Similarity	NPC104024
0.82	Intermediate Similarity	NPC65574
0.82	Intermediate Similarity	NPC101755
0.82	Intermediate Similarity	NPC304687
0.8194	Intermediate Similarity	NPC470990
0.8194	Intermediate Similarity	NPC224941
0.8194	Intermediate Similarity	NPC311430
0.8188	Intermediate Similarity	NPC223185
0.8182	Intermediate Similarity	NPC475468
0.8182	Intermediate Similarity	NPC55147
0.8182	Intermediate Similarity	NPC287504
0.8182	Intermediate Similarity	NPC54503
0.8176	Intermediate Similarity	NPC185607
0.8176	Intermediate Similarity	NPC297985
0.8176	Intermediate Similarity	NPC477884
0.8176	Intermediate Similarity	NPC474647
0.8176	Intermediate Similarity	NPC475953
0.817	Intermediate Similarity	NPC93498
0.817	Intermediate Similarity	NPC163883
0.8165	Intermediate Similarity	NPC249070
0.8165	Intermediate Similarity	NPC473445
0.8165	Intermediate Similarity	NPC42797
0.8163	Intermediate Similarity	NPC155552
0.8158	Intermediate Similarity	NPC177830
0.8158	Intermediate Similarity	NPC238366
0.8158	Intermediate Similarity	NPC474648
0.8158	Intermediate Similarity	NPC470916
0.8158	Intermediate Similarity	NPC477381
0.8156	Intermediate Similarity	NPC150809
0.8151	Intermediate Similarity	NPC471072

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 NPC46180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	881
0.2-0.3	1749
0.3-0.4	2578
0.4-0.5	1868
0.5-0.6	1103
0.6-0.7	508
0.7-0.8	136
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8146	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD5353	Approved
0.8038	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD37	Approved
0.7987	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4966	Approved
0.7962	Intermediate Similarity	NPD4965	Approved
0.7962	Intermediate Similarity	NPD4967	Phase 2
0.7898	Intermediate Similarity	NPD3817	Phase 2
0.7888	Intermediate Similarity	NPD5242	Approved
0.7867	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4110	Phase 3
0.7862	Intermediate Similarity	NPD6234	Discontinued
0.7848	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD230	Phase 1
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD3027	Phase 3
0.7771	Intermediate Similarity	NPD1934	Approved
0.777	Intermediate Similarity	NPD3748	Approved
0.7764	Intermediate Similarity	NPD8127	Discontinued
0.7756	Intermediate Similarity	NPD6599	Discontinued
0.7748	Intermediate Similarity	NPD4628	Phase 3
0.7737	Intermediate Similarity	NPD5536	Phase 2
0.7724	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6386	Approved
0.7707	Intermediate Similarity	NPD6385	Approved
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.764	Intermediate Similarity	NPD919	Approved
0.7636	Intermediate Similarity	NPD7228	Approved
0.7632	Intermediate Similarity	NPD8166	Discontinued
0.7625	Intermediate Similarity	NPD3882	Suspended
0.761	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD7819	Suspended
0.761	Intermediate Similarity	NPD2801	Approved
0.761	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6232	Discontinued
0.76	Intermediate Similarity	NPD2796	Approved
0.7597	Intermediate Similarity	NPD6799	Approved
0.7597	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5283	Phase 1
0.7546	Intermediate Similarity	NPD7199	Phase 2
0.753	Intermediate Similarity	NPD3818	Discontinued
0.7516	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5585	Approved
0.7485	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6873	Phase 2
0.7483	Intermediate Similarity	NPD2438	Suspended
0.7469	Intermediate Similarity	NPD7075	Discontinued
0.7468	Intermediate Similarity	NPD6190	Approved
0.7465	Intermediate Similarity	NPD3705	Approved
0.7456	Intermediate Similarity	NPD7240	Approved
0.7455	Intermediate Similarity	NPD3926	Phase 2
0.7455	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5402	Approved
0.745	Intermediate Similarity	NPD447	Suspended
0.745	Intermediate Similarity	NPD6355	Discontinued
0.7447	Intermediate Similarity	NPD17	Approved
0.7445	Intermediate Similarity	NPD1241	Discontinued
0.744	Intermediate Similarity	NPD7074	Phase 3
0.7439	Intermediate Similarity	NPD1247	Approved
0.7432	Intermediate Similarity	NPD8032	Phase 2
0.7413	Intermediate Similarity	NPD2981	Phase 2
0.741	Intermediate Similarity	NPD6166	Phase 2
0.741	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1653	Approved
0.7396	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1465	Phase 2
0.7388	Intermediate Similarity	NPD1358	Approved
0.7383	Intermediate Similarity	NPD2979	Phase 3
0.7381	Intermediate Similarity	NPD7054	Approved
0.7368	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD6100	Approved
0.7365	Intermediate Similarity	NPD1296	Phase 2
0.7361	Intermediate Similarity	NPD2983	Phase 2
0.7361	Intermediate Similarity	NPD2982	Phase 2
0.7361	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6111	Discontinued
0.7342	Intermediate Similarity	NPD920	Approved
0.7337	Intermediate Similarity	NPD7472	Approved
0.7329	Intermediate Similarity	NPD6801	Discontinued
0.7325	Intermediate Similarity	NPD2533	Approved
0.7325	Intermediate Similarity	NPD2532	Approved
0.7325	Intermediate Similarity	NPD2534	Approved
0.7313	Intermediate Similarity	NPD3134	Approved
0.7312	Intermediate Similarity	NPD4380	Phase 2
0.7312	Intermediate Similarity	NPD7028	Phase 2
0.731	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7124	Phase 2
0.7297	Intermediate Similarity	NPD7095	Approved
0.7292	Intermediate Similarity	NPD3972	Approved
0.7292	Intermediate Similarity	NPD1608	Approved
0.729	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3018	Phase 2
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1511	Approved
0.7261	Intermediate Similarity	NPD4357	Discontinued
0.726	Intermediate Similarity	NPD3267	Approved
0.726	Intermediate Similarity	NPD3266	Approved
0.7255	Intermediate Similarity	NPD2935	Discontinued
0.7254	Intermediate Similarity	NPD5691	Approved
0.7251	Intermediate Similarity	NPD7685	Pre-registration
0.7244	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4359	Approved
0.7233	Intermediate Similarity	NPD5403	Approved
0.723	Intermediate Similarity	NPD6832	Phase 2
0.7222	Intermediate Similarity	NPD1281	Approved
0.7219	Intermediate Similarity	NPD1933	Approved
0.7215	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD5401	Approved
0.7215	Intermediate Similarity	NPD3146	Approved
0.7211	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7808	Phase 3
0.7208	Intermediate Similarity	NPD7266	Discontinued
0.72	Intermediate Similarity	NPD6233	Phase 2
0.7195	Intermediate Similarity	NPD7768	Phase 2
0.719	Intermediate Similarity	NPD1510	Phase 2
0.719	Intermediate Similarity	NPD2799	Discontinued
0.7186	Intermediate Similarity	NPD7229	Phase 3
0.7171	Intermediate Similarity	NPD6653	Approved
0.717	Intermediate Similarity	NPD6273	Approved
0.717	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1512	Approved
0.7162	Intermediate Similarity	NPD9494	Approved
0.7161	Intermediate Similarity	NPD1549	Phase 2
0.716	Intermediate Similarity	NPD7411	Suspended
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1240	Approved
0.7151	Intermediate Similarity	NPD7251	Discontinued
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6798	Discontinued
0.7133	Intermediate Similarity	NPD9268	Approved
0.7133	Intermediate Similarity	NPD1651	Approved
0.7133	Intermediate Similarity	NPD3268	Approved
0.7126	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1652	Phase 2
0.7115	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1243	Approved
0.7115	Intermediate Similarity	NPD2800	Approved
0.7114	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5124	Phase 1
0.7105	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD422	Phase 1
0.7097	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6797	Phase 2
0.7092	Intermediate Similarity	NPD7157	Approved
0.7089	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4870	Approved
0.7083	Intermediate Similarity	NPD1778	Approved
0.7075	Intermediate Similarity	NPD1283	Approved
0.7075	Intermediate Similarity	NPD1876	Approved
0.7059	Intermediate Similarity	NPD1607	Approved
0.7059	Intermediate Similarity	NPD6651	Approved
0.7055	Intermediate Similarity	NPD9269	Phase 2
0.7052	Intermediate Similarity	NPD6559	Discontinued
0.7051	Intermediate Similarity	NPD4534	Discontinued
0.7047	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3496	Discontinued
0.7032	Intermediate Similarity	NPD2531	Phase 2
0.7032	Intermediate Similarity	NPD1551	Phase 2
0.7025	Intermediate Similarity	NPD3887	Approved
0.7018	Intermediate Similarity	NPD3751	Discontinued
0.7013	Intermediate Similarity	NPD7097	Phase 1
0.7011	Intermediate Similarity	NPD7549	Discontinued
0.7	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6005	Phase 3
0.6987	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6002	Phase 3
0.6987	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6004	Phase 3
0.698	Remote Similarity	NPD5647	Approved
0.6975	Remote Similarity	NPD3687	Approved
0.6975	Remote Similarity	NPD3686	Approved
0.6974	Remote Similarity	NPD4062	Phase 3
0.6966	Remote Similarity	NPD4626	Approved
0.6959	Remote Similarity	NPD8651	Approved
0.6951	Remote Similarity	NPD5090	Approved
0.6951	Remote Similarity	NPD5089	Approved
0.6946	Remote Similarity	NPD6971	Discontinued
0.6944	Remote Similarity	NPD9545	Approved
0.6943	Remote Similarity	NPD2424	Discontinued
0.6937	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5297	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