NPASS Compound

Structure

CID279379 OpenBabel06191716082D 29 30 0 0 1 0 0 0 0 0999 V2000 -0.8660 3.5000 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 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 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 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 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 2.5981 0.5000 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 -0.8660 1.5000 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 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 7 1 0 0 0 0 3 16 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 2 0 0 0 0 8 17 1 0 0 0 0 9 11 2 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 21 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 2 1 6 0 0 0 15 23 1 0 0 0 0 15 28 1 0 0 0 0 16 24 2 0 0 0 0 16 29 1 0 0 0 0 18 23 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 21 2 0 0 0 0 20 28 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 29 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.19
Volume:	420.901
LogP:	3.929
LogD:	3.539
LogS:	-5.203
# Rotatable Bonds:	10
TPSA:	63.22
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.563
Synthetic Accessibility Score:	3.172
Fsp3:	0.348
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:	-4.632
MDCK Permeability:	5.130523641128093e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.158

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.277
Plasma Protein Binding (PPB):	95.58458709716797%
Volume Distribution (VD):	1.21
Pgp-substrate:	4.930943012237549%

ADMET: Metabolism

CYP1A2-inhibitor:	0.275
CYP1A2-substrate:	0.859
CYP2C19-inhibitor:	0.839
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.758
CYP2C9-substrate:	0.38
CYP2D6-inhibitor:	0.461
CYP2D6-substrate:	0.645
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	5.549
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.463
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.299
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.079
Carcinogencity:	0.209
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC279379

Natural Product ID:	NPC279379
*Common Name:**	Ligraminol C
IUPAC Name:	[(1R,2R)-1-(3,4-dimethoxyphenyl)-2-[2-methoxy-4-[(Z)-prop-1-enyl]phenoxy]propyl] acetate
Synonyms:	Ligraminol C
Standard InCHIKey:	PYVVKTYHVHGNMI-ZJTDORCHSA-N
Standard InCHI:	InChI=1S/C23H28O6/c1-7-8-17-9-11-20(21(13-17)26-5)28-15(2)23(29-16(3)24)18-10-12-19(25-4)22(14-18)27-6/h7-15,23H,1-6H3/b8-7-/t15-,23+/m1/s1
SMILES:	C/C=Cc1ccc(c(c1)OC)O[C@@H]([C@@H](c1ccc(c(c1)OC)OC)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1928003
PubChem CID:	56599265
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
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22951040]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
Others	1

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9540.0	nM	PMID[546222]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000.0	nM	PMID[546222]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	>	10000.0	nM	PMID[546222]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	25930.0	nM	PMID[546222]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	16170.0	nM	PMID[546222]
NPT34	Cell Line	BV-2	Mus musculus	Activity	=	90.5	%	PMID[546222]

☑ 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 NPC279379 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	299
0.1-0.2	1439
0.2-0.3	4567
0.3-0.4	11574
0.4-0.5	6608
0.5-0.6	4368
0.6-0.7	9545
0.7-0.8	3573
0.8-0.85	592
0.85-0.9	115
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9587	High Similarity	NPC210674
0.9573	High Similarity	NPC267064
0.9431	High Similarity	NPC79184
0.9431	High Similarity	NPC307042
0.9431	High Similarity	NPC476399
0.9134	High Similarity	NPC309744
0.9098	High Similarity	NPC94276
0.9098	High Similarity	NPC109822
0.9091	High Similarity	NPC261661
0.9091	High Similarity	NPC71090
0.9062	High Similarity	NPC224941
0.9062	High Similarity	NPC311430
0.9016	High Similarity	NPC470887
0.9008	High Similarity	NPC65933
0.9008	High Similarity	NPC172676
0.9008	High Similarity	NPC216929
0.9008	High Similarity	NPC312713
0.9008	High Similarity	NPC126935
0.9008	High Similarity	NPC57268
0.8992	High Similarity	NPC277460
0.8992	High Similarity	NPC471719
0.896	High Similarity	NPC474651
0.896	High Similarity	NPC474623
0.8952	High Similarity	NPC191037
0.8952	High Similarity	NPC178284
0.8952	High Similarity	NPC58607
0.8926	High Similarity	NPC472596
0.8923	High Similarity	NPC126206
0.8889	High Similarity	NPC303522
0.888	High Similarity	NPC292056
0.888	High Similarity	NPC41706
0.888	High Similarity	NPC118787
0.888	High Similarity	NPC183181
0.888	High Similarity	NPC163332
0.888	High Similarity	NPC147821
0.888	High Similarity	NPC319625
0.888	High Similarity	NPC111247
0.888	High Similarity	NPC194841
0.888	High Similarity	NPC98745
0.8871	High Similarity	NPC194519
0.8846	High Similarity	NPC471664
0.8846	High Similarity	NPC471665
0.8837	High Similarity	NPC67247
0.8837	High Similarity	NPC135127
0.8837	High Similarity	NPC474600
0.8833	High Similarity	NPC159916
0.881	High Similarity	NPC31707
0.879	High Similarity	NPC114901
0.879	High Similarity	NPC34902
0.879	High Similarity	NPC293701
0.879	High Similarity	NPC48990
0.879	High Similarity	NPC121783
0.879	High Similarity	NPC18449
0.874	High Similarity	NPC470258
0.874	High Similarity	NPC285339
0.874	High Similarity	NPC202582
0.874	High Similarity	NPC273295
0.874	High Similarity	NPC222004
0.874	High Similarity	NPC3439
0.874	High Similarity	NPC226788
0.874	High Similarity	NPC218856
0.874	High Similarity	NPC190629
0.874	High Similarity	NPC86030
0.874	High Similarity	NPC5851
0.874	High Similarity	NPC210623
0.873	High Similarity	NPC474119
0.8718	High Similarity	NPC245552
0.8702	High Similarity	NPC286843
0.8702	High Similarity	NPC471988
0.8692	High Similarity	NPC476387
0.8692	High Similarity	NPC119060
0.8692	High Similarity	NPC249791
0.8692	High Similarity	NPC237594
0.8682	High Similarity	NPC319969
0.8682	High Similarity	NPC5423
0.8672	High Similarity	NPC19242
0.8667	High Similarity	NPC81067
0.8667	High Similarity	NPC9341
0.8661	High Similarity	NPC165128
0.8661	High Similarity	NPC226862
0.8661	High Similarity	NPC158471
0.8661	High Similarity	NPC57119
0.8661	High Similarity	NPC72529
0.8657	High Similarity	NPC473792
0.8657	High Similarity	NPC131971
0.8657	High Similarity	NPC473873
0.8651	High Similarity	NPC206882
0.8651	High Similarity	NPC213552
0.8651	High Similarity	NPC50683
0.8651	High Similarity	NPC127604
0.8651	High Similarity	NPC112571
0.8651	High Similarity	NPC285725
0.8651	High Similarity	NPC120225
0.8636	High Similarity	NPC281780
0.8632	High Similarity	NPC25067
0.8632	High Similarity	NPC88868
0.8632	High Similarity	NPC231251
0.8629	High Similarity	NPC288238
0.8626	High Similarity	NPC234865
0.8618	High Similarity	NPC471877
0.8615	High Similarity	NPC36437
0.8615	High Similarity	NPC241341
0.8615	High Similarity	NPC233018
0.8607	High Similarity	NPC254625
0.8607	High Similarity	NPC475961
0.8607	High Similarity	NPC37858
0.8605	High Similarity	NPC469625
0.8605	High Similarity	NPC469613
0.8605	High Similarity	NPC30043
0.8605	High Similarity	NPC472597
0.8594	High Similarity	NPC270849
0.8594	High Similarity	NPC26653
0.8594	High Similarity	NPC241354
0.8594	High Similarity	NPC476748
0.8583	High Similarity	NPC223807
0.8583	High Similarity	NPC474670
0.8571	High Similarity	NPC165106
0.8571	High Similarity	NPC289459
0.8561	High Similarity	NPC143895
0.856	High Similarity	NPC21238
0.856	High Similarity	NPC471693
0.855	High Similarity	NPC37065
0.855	High Similarity	NPC187194
0.855	High Similarity	NPC170779
0.855	High Similarity	NPC90083
0.8538	High Similarity	NPC35932
0.8538	High Similarity	NPC160991
0.8538	High Similarity	NPC16208
0.8538	High Similarity	NPC184447
0.8538	High Similarity	NPC230219
0.8538	High Similarity	NPC7903
0.8538	High Similarity	NPC245120
0.8538	High Similarity	NPC137669
0.8534	High Similarity	NPC258171
0.8529	High Similarity	NPC473090
0.8527	High Similarity	NPC477804
0.8527	High Similarity	NPC271208
0.8527	High Similarity	NPC469612
0.8527	High Similarity	NPC472338
0.8527	High Similarity	NPC469614
0.8527	High Similarity	NPC80600
0.8527	High Similarity	NPC233224
0.8527	High Similarity	NPC472024
0.8525	High Similarity	NPC474214
0.8516	High Similarity	NPC82862
0.8516	High Similarity	NPC252307
0.8516	High Similarity	NPC282703
0.8516	High Similarity	NPC45774
0.8516	High Similarity	NPC11258
0.8516	High Similarity	NPC245826
0.8516	High Similarity	NPC129570
0.8516	High Similarity	NPC222127
0.8516	High Similarity	NPC21867
0.8516	High Similarity	NPC474178
0.8516	High Similarity	NPC470084
0.8516	High Similarity	NPC184733
0.8516	High Similarity	NPC128208
0.8512	High Similarity	NPC123948
0.8504	High Similarity	NPC9891
0.8504	High Similarity	NPC88297
0.8504	High Similarity	NPC186845
0.8496	Intermediate Similarity	NPC865
0.8492	Intermediate Similarity	NPC246704
0.8485	Intermediate Similarity	NPC211386
0.8485	Intermediate Similarity	NPC214729
0.8473	Intermediate Similarity	NPC26394
0.8473	Intermediate Similarity	NPC263064
0.8467	Intermediate Similarity	NPC473909
0.8467	Intermediate Similarity	NPC163898
0.8467	Intermediate Similarity	NPC143120
0.8467	Intermediate Similarity	NPC274960
0.8462	Intermediate Similarity	NPC82111
0.8462	Intermediate Similarity	NPC473412
0.8462	Intermediate Similarity	NPC291837
0.8462	Intermediate Similarity	NPC469698
0.8462	Intermediate Similarity	NPC227160
0.8456	Intermediate Similarity	NPC478239
0.8455	Intermediate Similarity	NPC474320
0.8455	Intermediate Similarity	NPC135961
0.845	Intermediate Similarity	NPC83062
0.8438	Intermediate Similarity	NPC473092
0.8438	Intermediate Similarity	NPC242032
0.8438	Intermediate Similarity	NPC165045
0.8438	Intermediate Similarity	NPC210355
0.8438	Intermediate Similarity	NPC8050
0.8438	Intermediate Similarity	NPC118533
0.8438	Intermediate Similarity	NPC473093
0.8438	Intermediate Similarity	NPC474821
0.843	Intermediate Similarity	NPC47194
0.843	Intermediate Similarity	NPC475815
0.843	Intermediate Similarity	NPC473264
0.8425	Intermediate Similarity	NPC85830
0.8425	Intermediate Similarity	NPC148627
0.8421	Intermediate Similarity	NPC25695
0.8421	Intermediate Similarity	NPC172818
0.8421	Intermediate Similarity	NPC37468
0.8421	Intermediate Similarity	NPC11453
0.8413	Intermediate Similarity	NPC108545
0.8409	Intermediate Similarity	NPC193026
0.8409	Intermediate Similarity	NPC476411

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 NPC279379 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	903
0.2-0.3	1718
0.3-0.4	2635
0.4-0.5	1740
0.5-0.6	986
0.6-0.7	699
0.7-0.8	193
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD5283	Phase 1
0.84	Intermediate Similarity	NPD3705	Approved
0.8333	Intermediate Similarity	NPD5535	Approved
0.8308	Intermediate Similarity	NPD3027	Phase 3
0.8293	Intermediate Similarity	NPD5536	Phase 2
0.816	Intermediate Similarity	NPD5585	Approved
0.8067	Intermediate Similarity	NPD1358	Approved
0.8047	Intermediate Similarity	NPD2981	Phase 2
0.7986	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4110	Phase 3
0.7985	Intermediate Similarity	NPD1613	Approved
0.7985	Intermediate Similarity	NPD4060	Phase 1
0.7985	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD2982	Phase 2
0.7984	Intermediate Similarity	NPD2983	Phase 2
0.7955	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD17	Approved
0.791	Intermediate Similarity	NPD6233	Phase 2
0.7895	Intermediate Similarity	NPD7095	Approved
0.7891	Intermediate Similarity	NPD3496	Discontinued
0.7879	Intermediate Similarity	NPD3018	Phase 2
0.7851	Intermediate Similarity	NPD2684	Approved
0.7847	Intermediate Similarity	NPD3687	Approved
0.7847	Intermediate Similarity	NPD3686	Approved
0.7846	Intermediate Similarity	NPD4359	Approved
0.7846	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6798	Discontinued
0.7833	Intermediate Similarity	NPD3134	Approved
0.7832	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD228	Approved
0.7794	Intermediate Similarity	NPD4340	Discontinued
0.7794	Intermediate Similarity	NPD6355	Discontinued
0.7778	Intermediate Similarity	NPD4062	Phase 3
0.777	Intermediate Similarity	NPD3817	Phase 2
0.777	Intermediate Similarity	NPD7266	Discontinued
0.7769	Intermediate Similarity	NPD1608	Approved
0.7762	Intermediate Similarity	NPD3146	Approved
0.7762	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD2861	Phase 2
0.7744	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7843	Approved
0.7737	Intermediate Similarity	NPD2653	Approved
0.7734	Intermediate Similarity	NPD5691	Approved
0.773	Intermediate Similarity	NPD4628	Phase 3
0.7708	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7157	Approved
0.7698	Intermediate Similarity	NPD6032	Approved
0.7692	Intermediate Similarity	NPD1611	Approved
0.7687	Intermediate Similarity	NPD6386	Approved
0.7687	Intermediate Similarity	NPD6385	Approved
0.7674	Intermediate Similarity	NPD1778	Approved
0.7656	Intermediate Similarity	NPD1894	Discontinued
0.7647	Intermediate Similarity	NPD4870	Approved
0.7647	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD5762	Approved
0.7643	Intermediate Similarity	NPD1375	Discontinued
0.7643	Intermediate Similarity	NPD5763	Approved
0.7603	Intermediate Similarity	NPD1653	Approved
0.7597	Intermediate Similarity	NPD1357	Approved
0.7591	Intermediate Similarity	NPD1558	Phase 1
0.7591	Intermediate Similarity	NPD2979	Phase 3
0.7591	Intermediate Similarity	NPD4140	Approved
0.7571	Intermediate Similarity	NPD2438	Suspended
0.7554	Intermediate Similarity	NPD7097	Phase 1
0.7552	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4236	Phase 3
0.7535	Intermediate Similarity	NPD4162	Approved
0.7535	Intermediate Similarity	NPD4237	Approved
0.7534	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1934	Approved
0.7517	Intermediate Similarity	NPD37	Approved
0.7517	Intermediate Similarity	NPD4123	Phase 3
0.75	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4965	Approved
0.7483	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4210	Discontinued
0.7483	Intermediate Similarity	NPD4967	Phase 2
0.7483	Intermediate Similarity	NPD4966	Approved
0.7482	Intermediate Similarity	NPD6653	Approved
0.7481	Intermediate Similarity	NPD3847	Discontinued
0.7445	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD5111	Phase 2
0.7445	Intermediate Similarity	NPD5110	Phase 2
0.7445	Intermediate Similarity	NPD5109	Approved
0.7444	Intermediate Similarity	NPD5327	Phase 3
0.7432	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4538	Approved
0.7429	Intermediate Similarity	NPD4536	Approved
0.7426	Intermediate Similarity	NPD4908	Phase 1
0.7424	Intermediate Similarity	NPD1535	Discovery
0.7424	Intermediate Similarity	NPD422	Phase 1
0.7424	Intermediate Similarity	NPD1091	Approved
0.7424	Intermediate Similarity	NPD1281	Approved
0.7413	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6674	Discontinued
0.7413	Intermediate Similarity	NPD1652	Phase 2
0.7413	Intermediate Similarity	NPD3060	Approved
0.741	Intermediate Similarity	NPD1933	Approved
0.7405	Intermediate Similarity	NPD5846	Approved
0.7405	Intermediate Similarity	NPD4626	Approved
0.7405	Intermediate Similarity	NPD6516	Phase 2
0.7403	Intermediate Similarity	NPD7199	Phase 2
0.7403	Intermediate Similarity	NPD8127	Discontinued
0.7402	Intermediate Similarity	NPD1241	Discontinued
0.7398	Intermediate Similarity	NPD968	Approved
0.7388	Intermediate Similarity	NPD8651	Approved
0.7388	Intermediate Similarity	NPD2922	Phase 1
0.7386	Intermediate Similarity	NPD6234	Discontinued
0.7385	Intermediate Similarity	NPD1182	Approved
0.7385	Intermediate Similarity	NPD1548	Phase 1
0.7376	Intermediate Similarity	NPD7033	Discontinued
0.7372	Intermediate Similarity	NPD5163	Phase 2
0.7368	Intermediate Similarity	NPD1481	Phase 2
0.7364	Intermediate Similarity	NPD3596	Phase 2
0.7361	Intermediate Similarity	NPD6331	Phase 2
0.736	Intermediate Similarity	NPD5451	Approved
0.7351	Intermediate Similarity	NPD2801	Approved
0.7351	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4534	Discontinued
0.7342	Intermediate Similarity	NPD5844	Phase 1
0.7339	Intermediate Similarity	NPD290	Approved
0.7338	Intermediate Similarity	NPD5494	Approved
0.7329	Intermediate Similarity	NPD6799	Approved
0.7328	Intermediate Similarity	NPD1651	Approved
0.7324	Intermediate Similarity	NPD3539	Phase 1
0.7319	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5718	Phase 2
0.7317	Intermediate Similarity	NPD9697	Approved
0.731	Intermediate Similarity	NPD6190	Approved
0.731	Intermediate Similarity	NPD2677	Approved
0.7308	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6832	Phase 2
0.7293	Intermediate Similarity	NPD1610	Phase 2
0.7292	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6671	Approved
0.7286	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3657	Discovery
0.7286	Intermediate Similarity	NPD447	Suspended
0.7279	Intermediate Similarity	NPD3536	Discontinued
0.7279	Intermediate Similarity	NPD6584	Phase 3
0.7273	Intermediate Similarity	NPD3540	Phase 1
0.7267	Intermediate Similarity	NPD4675	Approved
0.7267	Intermediate Similarity	NPD4972	Discontinued
0.7267	Intermediate Similarity	NPD4678	Approved
0.7266	Intermediate Similarity	NPD3530	Approved
0.7266	Intermediate Similarity	NPD3531	Approved
0.7266	Intermediate Similarity	NPD8032	Phase 2
0.7266	Intermediate Similarity	NPD3532	Approved
0.7261	Intermediate Similarity	NPD4481	Phase 3
0.726	Intermediate Similarity	NPD5058	Phase 3
0.7259	Intermediate Similarity	NPD1283	Approved
0.7255	Intermediate Similarity	NPD3882	Suspended
0.7254	Intermediate Similarity	NPD5588	Approved
0.7254	Intermediate Similarity	NPD5960	Phase 3
0.7252	Intermediate Similarity	NPD6581	Approved
0.7252	Intermediate Similarity	NPD6580	Approved
0.7239	Intermediate Similarity	NPD1840	Phase 2
0.7239	Intermediate Similarity	NPD2231	Phase 2
0.7239	Intermediate Similarity	NPD2235	Phase 2
0.7226	Intermediate Similarity	NPD2237	Approved
0.7226	Intermediate Similarity	NPD5677	Discontinued
0.7222	Intermediate Similarity	NPD3021	Approved
0.7222	Intermediate Similarity	NPD5958	Discontinued
0.7222	Intermediate Similarity	NPD3022	Approved
0.7214	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3620	Phase 2
0.7213	Intermediate Similarity	NPD291	Approved
0.7211	Intermediate Similarity	NPD1774	Approved
0.7205	Intermediate Similarity	NPD7038	Approved
0.7205	Intermediate Similarity	NPD7039	Approved
0.7203	Intermediate Similarity	NPD2531	Phase 2
0.7203	Intermediate Similarity	NPD2796	Approved
0.7203	Intermediate Similarity	NPD2161	Phase 2
0.7197	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD5242	Approved
0.7192	Intermediate Similarity	NPD3887	Approved
0.719	Intermediate Similarity	NPD5353	Approved
0.719	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD821	Approved
0.7183	Intermediate Similarity	NPD6895	Approved
0.7183	Intermediate Similarity	NPD6896	Approved
0.7174	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD2614	Approved
0.7163	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5124	Phase 1
0.7163	Intermediate Similarity	NPD5735	Approved
0.7162	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD919	Approved
0.7154	Intermediate Similarity	NPD2557	Approved
0.7153	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6166	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data