NPASS Compound

Structure

NPC474979 OpenBabel07101719252D 26 28 0 0 1 0 0 0 0 0999 V2000 -4.6888 -4.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2575 -2.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7229 -3.9659 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 0.0000 -2.0000 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 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 0 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 -2.5981 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 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 2.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 20 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 16 2 0 0 0 0 16 21 1 0 0 0 0 17 21 1 6 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 2 0 0 0 0 19 26 1 0 0 0 0 20 2 1 6 0 0 0 21 3 1 6 0 0 0 22 4 1 1 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	388.014
LogP:	3.643
LogD:	1.995
LogS:	-4.513
# Rotatable Bonds:	5
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	4.566
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.292
MDCK Permeability:	3.158020263072103e-05
Pgp-inhibitor:	0.359
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.428
Plasma Protein Binding (PPB):	94.37914276123047%
Volume Distribution (VD):	0.27
Pgp-substrate:	3.1779003143310547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.271
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.647
CYP2C9-inhibitor:	0.157
CYP2C9-substrate:	0.599
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.258
CYP3A4-inhibitor:	0.448
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	1.014
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.163
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.877
Carcinogencity:	0.478
Eye Corrosion:	0.891
Eye Irritation:	0.815
Respiratory Toxicity:	0.378

Download Data

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

Natural Product: NPC474979

Natural Product ID:	NPC474979
*Common Name:**	19-Malonyloxy-Entisopimara-8(9),15-Diene
IUPAC Name:	3-[[(1R,4aR,7R,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,5,6,8,9,10,10a-octahydro-2H-phenanthren-1-yl]oxy]-3-oxopropanoic acid
Synonyms:
Standard InCHIKey:	NKRZOAWZBYVTMB-KVJIRVJXSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-5-20(2)12-9-16-15(14-20)7-8-17-21(16,3)10-6-11-22(17,4)26-19(25)13-18(23)24/h5,17H,1,6-14H2,2-4H3,(H,23,24)/t17-,20+,21-,22+/m0/s1
SMILES:	C=C[C@]1(C)CCC2=C(C1)CC[C@H]1[C@@]2(C)CCC[C@@]1(C)OC(=O)CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490701
PubChem CID:	44566221
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO33152	calceolaria pinifolia	Species	Calceolariaceae	Eukaryota	aerial part	46 km west of Puesto de Gendarmeria in the province of San Juan, Argentina (3021 S; 6940 W)	1997-Jan	PMID[12608857]

☑ 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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[463811]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[463811]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[463811]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	32.0	ug.mL-1	PMID[463811]

☑ 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 NPC474979 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	172
0.1-0.2	1242
0.2-0.3	5527
0.3-0.4	15592
0.4-0.5	9049
0.5-0.6	6881
0.6-0.7	3903
0.7-0.8	327
0.8-0.85	0
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9615	High Similarity	NPC473592
0.9481	High Similarity	NPC474978
0.9114	High Similarity	NPC476101
0.8235	Intermediate Similarity	NPC76333
0.8049	Intermediate Similarity	NPC321514
0.8046	Intermediate Similarity	NPC171722
0.8	Intermediate Similarity	NPC474789
0.8	Intermediate Similarity	NPC52108
0.7976	Intermediate Similarity	NPC142163
0.7976	Intermediate Similarity	NPC327002
0.7952	Intermediate Similarity	NPC100906
0.7935	Intermediate Similarity	NPC120708
0.7931	Intermediate Similarity	NPC262085
0.7931	Intermediate Similarity	NPC73038
0.7912	Intermediate Similarity	NPC78580
0.7912	Intermediate Similarity	NPC184006
0.7912	Intermediate Similarity	NPC23621
0.7907	Intermediate Similarity	NPC156981
0.7889	Intermediate Similarity	NPC477574
0.7882	Intermediate Similarity	NPC15910
0.7865	Intermediate Similarity	NPC469866
0.7865	Intermediate Similarity	NPC471342
0.7865	Intermediate Similarity	NPC59682
0.7857	Intermediate Similarity	NPC269791
0.7857	Intermediate Similarity	NPC37038
0.7841	Intermediate Similarity	NPC131329
0.7841	Intermediate Similarity	NPC245004
0.7831	Intermediate Similarity	NPC179028
0.7826	Intermediate Similarity	NPC23241
0.7826	Intermediate Similarity	NPC195715
0.7826	Intermediate Similarity	NPC473648
0.7791	Intermediate Similarity	NPC477373
0.7791	Intermediate Similarity	NPC476100
0.7791	Intermediate Similarity	NPC476927
0.7778	Intermediate Similarity	NPC148414
0.7778	Intermediate Similarity	NPC175628
0.7778	Intermediate Similarity	NPC71152
0.7778	Intermediate Similarity	NPC111585
0.7738	Intermediate Similarity	NPC327674
0.7738	Intermediate Similarity	NPC231431
0.7727	Intermediate Similarity	NPC474970
0.7727	Intermediate Similarity	NPC325594
0.7711	Intermediate Similarity	NPC132542
0.7711	Intermediate Similarity	NPC283619
0.7692	Intermediate Similarity	NPC36491
0.7692	Intermediate Similarity	NPC471588
0.7692	Intermediate Similarity	NPC26888
0.7692	Intermediate Similarity	NPC228784
0.7692	Intermediate Similarity	NPC6255
0.7692	Intermediate Similarity	NPC288833
0.7692	Intermediate Similarity	NPC282616
0.7692	Intermediate Similarity	NPC155120
0.7692	Intermediate Similarity	NPC324341
0.7692	Intermediate Similarity	NPC966
0.7683	Intermediate Similarity	NPC279666
0.7683	Intermediate Similarity	NPC192540
0.7674	Intermediate Similarity	NPC256112
0.7674	Intermediate Similarity	NPC73882
0.7667	Intermediate Similarity	NPC474889
0.7667	Intermediate Similarity	NPC30522
0.7667	Intermediate Similarity	NPC474700
0.7667	Intermediate Similarity	NPC474570
0.7667	Intermediate Similarity	NPC20946
0.7667	Intermediate Similarity	NPC16265
0.766	Intermediate Similarity	NPC26413
0.7647	Intermediate Similarity	NPC477057
0.7647	Intermediate Similarity	NPC104545
0.7619	Intermediate Similarity	NPC280654
0.7619	Intermediate Similarity	NPC260385
0.7619	Intermediate Similarity	NPC110094
0.7614	Intermediate Similarity	NPC476602
0.7614	Intermediate Similarity	NPC191965
0.7609	Intermediate Similarity	NPC131840
0.7609	Intermediate Similarity	NPC86368
0.7604	Intermediate Similarity	NPC473514
0.759	Intermediate Similarity	NPC69143
0.759	Intermediate Similarity	NPC104806
0.759	Intermediate Similarity	NPC309399
0.7582	Intermediate Similarity	NPC113989
0.7582	Intermediate Similarity	NPC473269
0.7582	Intermediate Similarity	NPC471896
0.7582	Intermediate Similarity	NPC120840
0.7582	Intermediate Similarity	NPC86372
0.7582	Intermediate Similarity	NPC474728
0.7582	Intermediate Similarity	NPC172361
0.7579	Intermediate Similarity	NPC164349
0.7561	Intermediate Similarity	NPC476046
0.7561	Intermediate Similarity	NPC161923
0.7561	Intermediate Similarity	NPC103958
0.7561	Intermediate Similarity	NPC283908
0.7561	Intermediate Similarity	NPC241854
0.7561	Intermediate Similarity	NPC251970
0.7561	Intermediate Similarity	NPC183503
0.7558	Intermediate Similarity	NPC20096
0.7558	Intermediate Similarity	NPC48673
0.7558	Intermediate Similarity	NPC142244
0.7558	Intermediate Similarity	NPC38350
0.7558	Intermediate Similarity	NPC201912
0.7558	Intermediate Similarity	NPC278459
0.7556	Intermediate Similarity	NPC72397
0.7556	Intermediate Similarity	NPC24816
0.7553	Intermediate Similarity	NPC98874
0.7553	Intermediate Similarity	NPC132824
0.7553	Intermediate Similarity	NPC269492
0.7553	Intermediate Similarity	NPC327788
0.7531	Intermediate Similarity	NPC160817
0.7531	Intermediate Similarity	NPC110799
0.7529	Intermediate Similarity	NPC199595
0.7528	Intermediate Similarity	NPC476104
0.7528	Intermediate Similarity	NPC137306
0.7528	Intermediate Similarity	NPC475181
0.7528	Intermediate Similarity	NPC324063
0.7528	Intermediate Similarity	NPC475753
0.7528	Intermediate Similarity	NPC84121
0.7527	Intermediate Similarity	NPC80365
0.7527	Intermediate Similarity	NPC222047
0.7527	Intermediate Similarity	NPC148964
0.7526	Intermediate Similarity	NPC473788
0.7526	Intermediate Similarity	NPC475558
0.75	Intermediate Similarity	NPC107039
0.75	Intermediate Similarity	NPC470590
0.75	Intermediate Similarity	NPC297265
0.75	Intermediate Similarity	NPC471899
0.75	Intermediate Similarity	NPC60755
0.75	Intermediate Similarity	NPC77099
0.75	Intermediate Similarity	NPC471897
0.75	Intermediate Similarity	NPC475156
0.75	Intermediate Similarity	NPC285184
0.75	Intermediate Similarity	NPC473576
0.75	Intermediate Similarity	NPC476417
0.7474	Intermediate Similarity	NPC21728
0.7474	Intermediate Similarity	NPC473456
0.7474	Intermediate Similarity	NPC89225
0.7473	Intermediate Similarity	NPC270768
0.7473	Intermediate Similarity	NPC234346
0.7473	Intermediate Similarity	NPC59263
0.7473	Intermediate Similarity	NPC61543
0.7473	Intermediate Similarity	NPC97577
0.7473	Intermediate Similarity	NPC475921
0.7473	Intermediate Similarity	NPC121798
0.7473	Intermediate Similarity	NPC263393
0.7473	Intermediate Similarity	NPC127689
0.7473	Intermediate Similarity	NPC225585
0.7473	Intermediate Similarity	NPC474704
0.7473	Intermediate Similarity	NPC130520
0.7473	Intermediate Similarity	NPC293048
0.7471	Intermediate Similarity	NPC260956
0.7471	Intermediate Similarity	NPC2524
0.7471	Intermediate Similarity	NPC286786
0.7447	Intermediate Similarity	NPC148523
0.7447	Intermediate Similarity	NPC777
0.7447	Intermediate Similarity	NPC171395
0.7444	Intermediate Similarity	NPC187376
0.7444	Intermediate Similarity	NPC158141
0.7444	Intermediate Similarity	NPC159046
0.7444	Intermediate Similarity	NPC96496
0.7444	Intermediate Similarity	NPC233836
0.7444	Intermediate Similarity	NPC231599
0.7444	Intermediate Similarity	NPC173089
0.7444	Intermediate Similarity	NPC166857
0.7442	Intermediate Similarity	NPC26139
0.7436	Intermediate Similarity	NPC474768
0.7423	Intermediate Similarity	NPC323441
0.7423	Intermediate Similarity	NPC476888
0.7423	Intermediate Similarity	NPC93744
0.7419	Intermediate Similarity	NPC118490
0.7419	Intermediate Similarity	NPC38232
0.7419	Intermediate Similarity	NPC298554
0.7416	Intermediate Similarity	NPC471344
0.7416	Intermediate Similarity	NPC474537
0.7416	Intermediate Similarity	NPC164424
0.7412	Intermediate Similarity	NPC74410
0.7412	Intermediate Similarity	NPC4827
0.7396	Intermediate Similarity	NPC174663
0.7391	Intermediate Similarity	NPC469400
0.7391	Intermediate Similarity	NPC111110
0.7391	Intermediate Similarity	NPC470589
0.7391	Intermediate Similarity	NPC130278
0.7391	Intermediate Similarity	NPC126369
0.7386	Intermediate Similarity	NPC200752
0.7386	Intermediate Similarity	NPC69279
0.7386	Intermediate Similarity	NPC23748
0.7386	Intermediate Similarity	NPC132386
0.7386	Intermediate Similarity	NPC49208
0.7386	Intermediate Similarity	NPC83569
0.7381	Intermediate Similarity	NPC89294
0.7381	Intermediate Similarity	NPC899
0.7381	Intermediate Similarity	NPC180886
0.7375	Intermediate Similarity	NPC94192
0.7368	Intermediate Similarity	NPC327179
0.7368	Intermediate Similarity	NPC167193
0.7368	Intermediate Similarity	NPC469528
0.7368	Intermediate Similarity	NPC472806
0.7368	Intermediate Similarity	NPC201657
0.7368	Intermediate Similarity	NPC471153
0.7368	Intermediate Similarity	NPC469369
0.7363	Intermediate Similarity	NPC242864
0.7363	Intermediate Similarity	NPC1753
0.7363	Intermediate Similarity	NPC474511
0.7363	Intermediate Similarity	NPC246708

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 NPC474979 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1682
0.2-0.3	4070
0.3-0.4	2261
0.4-0.5	595
0.5-0.6	248
0.6-0.7	141
0.7-0.8	4
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
0.7692	Intermediate Similarity	NPD6411	Approved
0.7473	Intermediate Similarity	NPD6101	Approved
0.7473	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7748	Approved
0.7333	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5695	Phase 3
0.7253	Intermediate Similarity	NPD3573	Approved
0.7128	Intermediate Similarity	NPD5284	Approved
0.7128	Intermediate Similarity	NPD5281	Approved
0.7128	Intermediate Similarity	NPD7515	Phase 2
0.7126	Intermediate Similarity	NPD7645	Phase 2
0.7113	Intermediate Similarity	NPD6083	Phase 2
0.7113	Intermediate Similarity	NPD7902	Approved
0.7113	Intermediate Similarity	NPD6084	Phase 2
0.7097	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5779	Approved
0.7053	Intermediate Similarity	NPD6399	Phase 3
0.7053	Intermediate Similarity	NPD5778	Approved
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6961	Remote Similarity	NPD5739	Approved
0.6961	Remote Similarity	NPD7128	Approved
0.6961	Remote Similarity	NPD6675	Approved
0.6961	Remote Similarity	NPD6402	Approved
0.6957	Remote Similarity	NPD6098	Approved
0.6947	Remote Similarity	NPD6050	Approved
0.6947	Remote Similarity	NPD5694	Approved
0.6941	Remote Similarity	NPD4785	Approved
0.6941	Remote Similarity	NPD4784	Approved
0.6932	Remote Similarity	NPD4195	Approved
0.6915	Remote Similarity	NPD6673	Approved
0.6915	Remote Similarity	NPD6904	Approved
0.6915	Remote Similarity	NPD6080	Approved
0.6907	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4243	Approved
0.6893	Remote Similarity	NPD5697	Approved
0.6869	Remote Similarity	NPD5696	Approved
0.6869	Remote Similarity	NPD7638	Approved
0.6869	Remote Similarity	NPD4225	Approved
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6857	Remote Similarity	NPD7102	Approved
0.6854	Remote Similarity	NPD7525	Registered
0.6842	Remote Similarity	NPD5692	Phase 3
0.6842	Remote Similarity	NPD5207	Approved
0.6827	Remote Similarity	NPD7320	Approved
0.6809	Remote Similarity	NPD6672	Approved
0.6809	Remote Similarity	NPD5737	Approved
0.6804	Remote Similarity	NPD7900	Approved
0.6804	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7640	Approved
0.68	Remote Similarity	NPD7639	Approved
0.6792	Remote Similarity	NPD6650	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6847	Approved
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6649	Approved
0.6789	Remote Similarity	NPD7115	Discovery
0.6774	Remote Similarity	NPD5690	Phase 2
0.6774	Remote Similarity	NPD6409	Approved
0.6774	Remote Similarity	NPD6684	Approved
0.6774	Remote Similarity	NPD5330	Approved
0.6774	Remote Similarity	NPD7521	Approved
0.6774	Remote Similarity	NPD7146	Approved
0.6774	Remote Similarity	NPD7334	Approved
0.6771	Remote Similarity	NPD7637	Suspended
0.6762	Remote Similarity	NPD6373	Approved
0.6762	Remote Similarity	NPD6372	Approved
0.6762	Remote Similarity	NPD6013	Approved
0.6762	Remote Similarity	NPD6014	Approved
0.6762	Remote Similarity	NPD6012	Approved
0.6737	Remote Similarity	NPD6051	Approved
0.6731	Remote Similarity	NPD5701	Approved
0.6729	Remote Similarity	NPD8297	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6703	Remote Similarity	NPD4221	Approved
0.6703	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6633	Remote Similarity	NPD6001	Approved
0.6632	Remote Similarity	NPD6903	Approved
0.6632	Remote Similarity	NPD5208	Approved
0.6632	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6079	Approved
0.6598	Remote Similarity	NPD8034	Phase 2
0.6598	Remote Similarity	NPD5693	Phase 1
0.6598	Remote Similarity	NPD8035	Phase 2
0.6596	Remote Similarity	NPD4623	Approved
0.6596	Remote Similarity	NPD4694	Approved
0.6596	Remote Similarity	NPD5280	Approved
0.6596	Remote Similarity	NPD3618	Phase 1
0.6596	Remote Similarity	NPD4519	Discontinued
0.6593	Remote Similarity	NPD4139	Approved
0.6593	Remote Similarity	NPD4692	Approved
0.6566	Remote Similarity	NPD5654	Approved
0.6562	Remote Similarity	NPD5328	Approved
0.6562	Remote Similarity	NPD4753	Phase 2
0.6559	Remote Similarity	NPD4197	Approved
0.6559	Remote Similarity	NPD4786	Approved
0.6522	Remote Similarity	NPD3667	Approved
0.6509	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1694	Approved
0.6481	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5275	Approved
0.6477	Remote Similarity	NPD7339	Approved
0.6477	Remote Similarity	NPD6942	Approved
0.6477	Remote Similarity	NPD4190	Phase 3
0.6471	Remote Similarity	NPD5285	Approved
0.6471	Remote Similarity	NPD5286	Approved
0.6471	Remote Similarity	NPD4696	Approved
0.646	Remote Similarity	NPD6319	Approved
0.6449	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3617	Approved
0.6436	Remote Similarity	NPD4755	Approved
0.6436	Remote Similarity	NPD5959	Approved
0.6421	Remote Similarity	NPD4689	Approved
0.6421	Remote Similarity	NPD4693	Phase 3
0.6421	Remote Similarity	NPD4688	Approved
0.6421	Remote Similarity	NPD5205	Approved
0.6421	Remote Similarity	NPD4690	Approved
0.6421	Remote Similarity	NPD4138	Approved
0.6404	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5210	Approved
0.64	Remote Similarity	NPD4629	Approved
0.6383	Remote Similarity	NPD3666	Approved
0.6383	Remote Similarity	NPD3133	Approved
0.6383	Remote Similarity	NPD3665	Phase 1
0.6379	Remote Similarity	NPD7492	Approved
0.6372	Remote Similarity	NPD7100	Approved
0.6372	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD4202	Approved
0.6346	Remote Similarity	NPD7632	Discontinued
0.6346	Remote Similarity	NPD4633	Approved
0.6346	Remote Similarity	NPD5224	Approved
0.6346	Remote Similarity	NPD5211	Phase 2
0.6346	Remote Similarity	NPD5225	Approved
0.6346	Remote Similarity	NPD5226	Approved
0.6344	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5222	Approved
0.6337	Remote Similarity	NPD5221	Approved
0.6337	Remote Similarity	NPD7732	Phase 3
0.6325	Remote Similarity	NPD6616	Approved
0.6316	Remote Similarity	NPD6054	Approved
0.6311	Remote Similarity	NPD4700	Approved
0.6304	Remote Similarity	NPD4748	Discontinued
0.63	Remote Similarity	NPD5707	Approved
0.6296	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD8264	Approved
0.6286	Remote Similarity	NPD5175	Approved
0.6286	Remote Similarity	NPD5174	Approved
0.6283	Remote Similarity	NPD6335	Approved
0.6277	Remote Similarity	NPD6695	Phase 3
0.6275	Remote Similarity	NPD5173	Approved
0.6271	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD6274	Approved
0.625	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4634	Approved
0.6237	Remote Similarity	NPD5369	Approved
0.6226	Remote Similarity	NPD5141	Approved
0.6218	Remote Similarity	NPD7736	Approved
0.6216	Remote Similarity	NPD4632	Approved
0.6211	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD3668	Phase 3
0.6207	Remote Similarity	NPD6370	Approved
0.62	Remote Similarity	NPD5133	Approved
0.6195	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6317	Approved
0.618	Remote Similarity	NPD6926	Approved
0.618	Remote Similarity	NPD6924	Approved
0.6176	Remote Similarity	NPD4697	Phase 3
0.6174	Remote Similarity	NPD6059	Approved
0.6168	Remote Similarity	NPD6008	Approved
0.6162	Remote Similarity	NPD4096	Approved
0.6154	Remote Similarity	NPD6404	Discontinued
0.6154	Remote Similarity	NPD8328	Phase 3
0.614	Remote Similarity	NPD6313	Approved
0.614	Remote Similarity	NPD6314	Approved
0.6134	Remote Similarity	NPD8293	Discontinued
0.6132	Remote Similarity	NPD6052	Approved
0.6122	Remote Similarity	NPD4518	Approved
0.6121	Remote Similarity	NPD6908	Approved
0.6121	Remote Similarity	NPD6015	Approved
0.6121	Remote Similarity	NPD6909	Approved
0.6121	Remote Similarity	NPD7503	Approved
0.6121	Remote Similarity	NPD6016	Approved
0.6111	Remote Similarity	NPD6412	Phase 2
0.6111	Remote Similarity	NPD6614	Approved
0.6111	Remote Similarity	NPD8039	Approved
0.6095	Remote Similarity	NPD5344	Discontinued
0.6068	Remote Similarity	NPD5988	Approved
0.6055	Remote Similarity	NPD4729	Approved
0.6055	Remote Similarity	NPD4730	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