NPASS Compound

Structure

NPC49320 OpenBabel07101719512D 34 38 0 0 1 0 0 0 0 0999 V2000 7.1870 -1.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7216 -2.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 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 2.5981 -2.5000 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 2.5981 0.5000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 1.0000 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 1.5000 0.0000 C 0 0 2 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 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 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 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 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 20 2 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 30 1 0 0 0 0 16 18 1 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 17 25 1 0 0 0 0 18 23 1 0 0 0 0 18 31 1 6 0 0 0 19 26 1 0 0 0 0 19 29 1 1 0 0 0 20 27 1 0 0 0 0 20 28 1 0 0 0 0 21 27 1 1 0 0 0 21 29 1 0 0 0 0 22 28 1 6 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 1 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	4.946
LogD:	3.997
LogS:	-4.489
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	5.031
Fsp3:	0.9
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:	-5.346
MDCK Permeability:	1.4176977856550366e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.072
30% Bioavailability (F30%):	0.551

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	96.09236145019531%
Volume Distribution (VD):	0.745
Pgp-substrate:	3.2016773223876953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.819
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.897
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.119

ADMET: Excretion

Clearance (CL):	1.484
Half-life (T1/2):	0.325

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.41
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.464
Maximum Recommended Daily Dose:	0.862
Skin Sensitization:	0.076
Carcinogencity:	0.024
Eye Corrosion:	0.177
Eye Irritation:	0.249
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC49320

Natural Product ID:	NPC49320
*Common Name:**	2Alpha-Hydroxymaprounic Acid
IUPAC Name:	(4aS,6aR,6bR,8aR,10R,11R,12aR,14aS,14bS)-10,11-dihydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,6a,7,8,8a,10,11,12,13,14,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	2Alpha-Hydroxymaprounic Acid
Standard InCHIKey:	JMJVYEINATYJHM-KLXPJGLFSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-25(2)14-15-30(24(33)34)13-10-20-27(5)11-8-19-26(3,4)23(32)18(31)16-29(19,7)21(27)9-12-28(20,6)22(30)17-25/h10,18-19,21-23,31-32H,8-9,11-17H2,1-7H3,(H,33,34)/t18-,19+,21+,22+,23+,27+,28-,29+,30-/m1/s1
SMILES:	O[C@@H]1C[C@]2(C)[C@H]3CC[C@@]4(C(=CC[C@@]5([C@H]4CC(C)(C)CC5)C(=O)O)[C@]3(C)CC[C@H]2C([C@H]1O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469925
PubChem CID:	44575645
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075783]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6631436]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[7515410]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7515410]
NPO27192	Maprounea africana	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7561895]
NPO27192	Maprounea africana	Species	Euphorbiaceae	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	2

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	=	3400.0	nM	PMID[520399]
NPT2	Others	Unspecified		IC50	=	56700.0	nM	PMID[520399]

☑ 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 NPC49320 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	220
0.1-0.2	1396
0.2-0.3	5025
0.3-0.4	14597
0.4-0.5	9012
0.5-0.6	5153
0.6-0.7	4772
0.7-0.8	1836
0.8-0.85	363
0.85-0.9	123
0.9-0.95	170
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
0.9882	High Similarity	NPC300351
0.9882	High Similarity	NPC71074
0.9882	High Similarity	NPC52021
0.9882	High Similarity	NPC84319
0.9882	High Similarity	NPC472149
0.9882	High Similarity	NPC25299
0.9882	High Similarity	NPC235884
0.9882	High Similarity	NPC306541
0.9767	High Similarity	NPC307335
0.9767	High Similarity	NPC275809
0.9767	High Similarity	NPC136313
0.9767	High Similarity	NPC74855
0.9655	High Similarity	NPC88116
0.9655	High Similarity	NPC32407
0.9655	High Similarity	NPC263548
0.9655	High Similarity	NPC20235
0.9655	High Similarity	NPC231063
0.9655	High Similarity	NPC145667
0.9655	High Similarity	NPC299996
0.9655	High Similarity	NPC282395
0.9545	High Similarity	NPC198245
0.9545	High Similarity	NPC96916
0.954	High Similarity	NPC474806
0.954	High Similarity	NPC133579
0.9529	High Similarity	NPC182797
0.9529	High Similarity	NPC52169
0.9524	High Similarity	NPC72638
0.9438	High Similarity	NPC201657
0.9438	High Similarity	NPC25848
0.9438	High Similarity	NPC307282
0.9438	High Similarity	NPC204961
0.9438	High Similarity	NPC158371
0.9438	High Similarity	NPC19376
0.9438	High Similarity	NPC259733
0.9438	High Similarity	NPC305464
0.9438	High Similarity	NPC230151
0.9438	High Similarity	NPC73004
0.9438	High Similarity	NPC173744
0.9438	High Similarity	NPC207922
0.9432	High Similarity	NPC188102
0.9432	High Similarity	NPC87095
0.9419	High Similarity	NPC234346
0.9419	High Similarity	NPC290972
0.9419	High Similarity	NPC59263
0.9419	High Similarity	NPC61543
0.9419	High Similarity	NPC121798
0.9419	High Similarity	NPC64872
0.9419	High Similarity	NPC263393
0.9419	High Similarity	NPC270768
0.9419	High Similarity	NPC225585
0.9419	High Similarity	NPC127689
0.9419	High Similarity	NPC293048
0.9419	High Similarity	NPC130520
0.9419	High Similarity	NPC274330
0.9419	High Similarity	NPC25906
0.9419	High Similarity	NPC198664
0.9419	High Similarity	NPC143232
0.9412	High Similarity	NPC68160
0.9412	High Similarity	NPC242468
0.9412	High Similarity	NPC51700
0.9412	High Similarity	NPC88716
0.9412	High Similarity	NPC18064
0.9412	High Similarity	NPC307426
0.9412	High Similarity	NPC102683
0.9412	High Similarity	NPC130577
0.9412	High Similarity	NPC98442
0.9412	High Similarity	NPC171203
0.9412	High Similarity	NPC293564
0.9412	High Similarity	NPC142415
0.9333	High Similarity	NPC259788
0.9333	High Similarity	NPC261935
0.9333	High Similarity	NPC43686
0.9333	High Similarity	NPC247139
0.9333	High Similarity	NPC9613
0.9333	High Similarity	NPC106112
0.9333	High Similarity	NPC255589
0.9326	High Similarity	NPC32118
0.931	High Similarity	NPC273621
0.931	High Similarity	NPC210037
0.931	High Similarity	NPC126369
0.931	High Similarity	NPC130278
0.931	High Similarity	NPC111110
0.931	High Similarity	NPC290614
0.931	High Similarity	NPC7260
0.931	High Similarity	NPC18872
0.931	High Similarity	NPC227467
0.931	High Similarity	NPC470589
0.931	High Similarity	NPC291028
0.931	High Similarity	NPC120968
0.931	High Similarity	NPC477872
0.9302	High Similarity	NPC181225
0.9302	High Similarity	NPC470629
0.9302	High Similarity	NPC474512
0.9302	High Similarity	NPC473242
0.9302	High Similarity	NPC290690
0.9302	High Similarity	NPC246708
0.9302	High Similarity	NPC40552
0.9302	High Similarity	NPC17733
0.9231	High Similarity	NPC29765
0.9231	High Similarity	NPC188833
0.9231	High Similarity	NPC271614
0.9231	High Similarity	NPC111214
0.9222	High Similarity	NPC88847
0.9213	High Similarity	NPC296164
0.9205	High Similarity	NPC288833
0.9205	High Similarity	NPC282616
0.9205	High Similarity	NPC158030
0.9205	High Similarity	NPC187722
0.9205	High Similarity	NPC228784
0.9205	High Similarity	NPC65120
0.9205	High Similarity	NPC4036
0.9205	High Similarity	NPC474525
0.9205	High Similarity	NPC324341
0.9205	High Similarity	NPC105189
0.9205	High Similarity	NPC155120
0.9205	High Similarity	NPC475708
0.9205	High Similarity	NPC966
0.9205	High Similarity	NPC145067
0.9205	High Similarity	NPC233455
0.9195	High Similarity	NPC470588
0.9195	High Similarity	NPC30522
0.9195	High Similarity	NPC161751
0.9195	High Similarity	NPC95246
0.9195	High Similarity	NPC474972
0.913	High Similarity	NPC35239
0.9121	High Similarity	NPC203343
0.9121	High Similarity	NPC312075
0.9101	High Similarity	NPC272075
0.9101	High Similarity	NPC158059
0.9101	High Similarity	NPC295643
0.9101	High Similarity	NPC86368
0.9101	High Similarity	NPC229281
0.9101	High Similarity	NPC118519
0.9101	High Similarity	NPC202728
0.9101	High Similarity	NPC298554
0.9101	High Similarity	NPC214756
0.9091	High Similarity	NPC474728
0.9091	High Similarity	NPC113989
0.9091	High Similarity	NPC172361
0.9091	High Similarity	NPC46441
0.9091	High Similarity	NPC193750
0.9091	High Similarity	NPC120840
0.9091	High Similarity	NPC86372
0.9059	High Similarity	NPC171789
0.9032	High Similarity	NPC233012
0.9032	High Similarity	NPC256247
0.9032	High Similarity	NPC54909
0.9	High Similarity	NPC222047
0.9	High Similarity	NPC191412
0.9	High Similarity	NPC114159
0.9	High Similarity	NPC159365
0.9	High Similarity	NPC474529
0.9	High Similarity	NPC209868
0.9	High Similarity	NPC91010
0.9	High Similarity	NPC6818
0.8989	High Similarity	NPC189520
0.8989	High Similarity	NPC60755
0.8989	High Similarity	NPC6255
0.8989	High Similarity	NPC285184
0.8989	High Similarity	NPC471588
0.8989	High Similarity	NPC77099
0.8989	High Similarity	NPC470590
0.8989	High Similarity	NPC38754
0.8977	High Similarity	NPC474686
0.8966	High Similarity	NPC71507
0.8953	High Similarity	NPC133954
0.8901	High Similarity	NPC473240
0.8901	High Similarity	NPC148523
0.8901	High Similarity	NPC474727
0.8901	High Similarity	NPC139570
0.8889	High Similarity	NPC63118
0.8889	High Similarity	NPC118490
0.8889	High Similarity	NPC49776
0.8889	High Similarity	NPC474436
0.8851	High Similarity	NPC475862
0.8851	High Similarity	NPC213412
0.8851	High Similarity	NPC73038
0.8851	High Similarity	NPC95594
0.8851	High Similarity	NPC235341
0.8851	High Similarity	NPC324063
0.8851	High Similarity	NPC477579
0.8851	High Similarity	NPC74363
0.8851	High Similarity	NPC56588
0.8804	High Similarity	NPC476327
0.8804	High Similarity	NPC157113
0.8804	High Similarity	NPC116457
0.8804	High Similarity	NPC327179
0.8804	High Similarity	NPC132824
0.8804	High Similarity	NPC98874
0.8804	High Similarity	NPC476318
0.8804	High Similarity	NPC62516
0.8791	High Similarity	NPC23621
0.8791	High Similarity	NPC60692
0.8791	High Similarity	NPC184006
0.8791	High Similarity	NPC74751
0.8791	High Similarity	NPC80365
0.8791	High Similarity	NPC78580
0.8778	High Similarity	NPC301244
0.8764	High Similarity	NPC220498
0.8764	High Similarity	NPC281524

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 NPC49320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1818
0.2-0.3	3854
0.3-0.4	2241
0.4-0.5	612
0.5-0.6	205
0.6-0.7	188
0.7-0.8	35
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9205	High Similarity	NPD7515	Phase 2
0.8791	High Similarity	NPD7748	Approved
0.8511	High Similarity	NPD7902	Approved
0.8315	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD7900	Approved
0.8046	Intermediate Similarity	NPD7645	Phase 2
0.7826	Intermediate Similarity	NPD3618	Phase 1
0.7802	Intermediate Similarity	NPD4786	Approved
0.7789	Intermediate Similarity	NPD8034	Phase 2
0.7789	Intermediate Similarity	NPD8035	Phase 2
0.7778	Intermediate Similarity	NPD3667	Approved
0.7766	Intermediate Similarity	NPD5328	Approved
0.7766	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6399	Phase 3
0.7692	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD6079	Approved
0.75	Intermediate Similarity	NPD6117	Approved
0.75	Intermediate Similarity	NPD7638	Approved
0.7474	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7639	Approved
0.7426	Intermediate Similarity	NPD7640	Approved
0.7419	Intermediate Similarity	NPD3665	Phase 1
0.7419	Intermediate Similarity	NPD3133	Approved
0.7419	Intermediate Similarity	NPD3666	Approved
0.7416	Intermediate Similarity	NPD6116	Phase 1
0.7404	Intermediate Similarity	NPD7128	Approved
0.7404	Intermediate Similarity	NPD6402	Approved
0.7404	Intermediate Similarity	NPD5739	Approved
0.7404	Intermediate Similarity	NPD6675	Approved
0.7364	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7525	Registered
0.7347	Intermediate Similarity	NPD4202	Approved
0.7333	Intermediate Similarity	NPD6114	Approved
0.7333	Intermediate Similarity	NPD6697	Approved
0.7333	Intermediate Similarity	NPD6115	Approved
0.7333	Intermediate Similarity	NPD6118	Approved
0.73	Intermediate Similarity	NPD7614	Phase 1
0.73	Intermediate Similarity	NPD5222	Approved
0.73	Intermediate Similarity	NPD4697	Phase 3
0.73	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5221	Approved
0.7281	Intermediate Similarity	NPD8328	Phase 3
0.7273	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7320	Approved
0.7264	Intermediate Similarity	NPD6881	Approved
0.7264	Intermediate Similarity	NPD6899	Approved
0.7263	Intermediate Similarity	NPD6409	Approved
0.7263	Intermediate Similarity	NPD5330	Approved
0.7263	Intermediate Similarity	NPD6684	Approved
0.7263	Intermediate Similarity	NPD7334	Approved
0.7263	Intermediate Similarity	NPD7521	Approved
0.7263	Intermediate Similarity	NPD7146	Approved
0.7245	Intermediate Similarity	NPD6411	Approved
0.7234	Intermediate Similarity	NPD3668	Phase 3
0.7228	Intermediate Similarity	NPD6083	Phase 2
0.7228	Intermediate Similarity	NPD4755	Approved
0.7228	Intermediate Similarity	NPD6084	Phase 2
0.7228	Intermediate Similarity	NPD5173	Approved
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7196	Intermediate Similarity	NPD6372	Approved
0.7196	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6373	Approved
0.7188	Intermediate Similarity	NPD3573	Approved
0.717	Intermediate Similarity	NPD5697	Approved
0.717	Intermediate Similarity	NPD5701	Approved
0.7156	Intermediate Similarity	NPD8297	Approved
0.713	Intermediate Similarity	NPD6883	Approved
0.713	Intermediate Similarity	NPD7102	Approved
0.713	Intermediate Similarity	NPD7290	Approved
0.7113	Intermediate Similarity	NPD6903	Approved
0.7113	Intermediate Similarity	NPD6672	Approved
0.7113	Intermediate Similarity	NPD5737	Approved
0.7103	Intermediate Similarity	NPD6011	Approved
0.7091	Intermediate Similarity	NPD4632	Approved
0.7087	Intermediate Similarity	NPD5285	Approved
0.7087	Intermediate Similarity	NPD5286	Approved
0.7087	Intermediate Similarity	NPD4700	Approved
0.7087	Intermediate Similarity	NPD4696	Approved
0.7083	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6649	Approved
0.7064	Intermediate Similarity	NPD8130	Phase 1
0.7064	Intermediate Similarity	NPD6847	Approved
0.7064	Intermediate Similarity	NPD6617	Approved
0.7064	Intermediate Similarity	NPD6869	Approved
0.7064	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6650	Approved
0.7041	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4753	Phase 2
0.7041	Intermediate Similarity	NPD6101	Approved
0.7037	Intermediate Similarity	NPD6013	Approved
0.7037	Intermediate Similarity	NPD6012	Approved
0.7037	Intermediate Similarity	NPD6014	Approved
0.7019	Intermediate Similarity	NPD5223	Approved
0.7009	Intermediate Similarity	NPD6412	Phase 2
0.7	Intermediate Similarity	NPD6942	Approved
0.7	Intermediate Similarity	NPD7339	Approved
0.7	Intermediate Similarity	NPD6882	Approved
0.699	Remote Similarity	NPD4225	Approved
0.6989	Remote Similarity	NPD4695	Discontinued
0.6961	Remote Similarity	NPD7732	Phase 3
0.6952	Remote Similarity	NPD5224	Approved
0.6952	Remote Similarity	NPD5211	Phase 2
0.6952	Remote Similarity	NPD5225	Approved
0.6952	Remote Similarity	NPD4633	Approved
0.6952	Remote Similarity	NPD5226	Approved
0.6952	Remote Similarity	NPD7632	Discontinued
0.6944	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5279	Phase 3
0.6887	Remote Similarity	NPD5175	Approved
0.6887	Remote Similarity	NPD4754	Approved
0.6887	Remote Similarity	NPD5174	Approved
0.6863	Remote Similarity	NPD5695	Phase 3
0.6863	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4221	Approved
0.6842	Remote Similarity	NPD4223	Phase 3
0.6827	Remote Similarity	NPD5696	Approved
0.6822	Remote Similarity	NPD5141	Approved
0.6818	Remote Similarity	NPD4634	Approved
0.6818	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6868	Approved
0.6804	Remote Similarity	NPD5329	Approved
0.6789	Remote Similarity	NPD6686	Approved
0.6786	Remote Similarity	NPD8133	Approved
0.6774	Remote Similarity	NPD3617	Approved
0.6771	Remote Similarity	NPD4788	Approved
0.6759	Remote Similarity	NPD4768	Approved
0.6759	Remote Similarity	NPD4767	Approved
0.6754	Remote Similarity	NPD6009	Approved
0.6735	Remote Similarity	NPD6098	Approved
0.6733	Remote Similarity	NPD5281	Approved
0.6733	Remote Similarity	NPD5284	Approved
0.6724	Remote Similarity	NPD6319	Approved
0.6723	Remote Similarity	NPD7507	Approved
0.6701	Remote Similarity	NPD4197	Approved
0.67	Remote Similarity	NPD6080	Approved
0.67	Remote Similarity	NPD6673	Approved
0.67	Remote Similarity	NPD6904	Approved
0.6699	Remote Similarity	NPD5210	Approved
0.6699	Remote Similarity	NPD4629	Approved
0.6696	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6638	Remote Similarity	NPD7101	Approved
0.6638	Remote Similarity	NPD7100	Approved
0.6636	Remote Similarity	NPD5128	Approved
0.6636	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD4729	Approved
0.6636	Remote Similarity	NPD4730	Approved
0.6633	Remote Similarity	NPD1694	Approved
0.663	Remote Similarity	NPD3703	Phase 2
0.6612	Remote Similarity	NPD7736	Approved
0.6609	Remote Similarity	NPD6317	Approved
0.6606	Remote Similarity	NPD6008	Approved
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4688	Approved
0.6566	Remote Similarity	NPD4690	Approved
0.6566	Remote Similarity	NPD5205	Approved
0.6566	Remote Similarity	NPD4693	Phase 3
0.6566	Remote Similarity	NPD4519	Discontinued
0.6566	Remote Similarity	NPD4689	Approved
0.6566	Remote Similarity	NPD4623	Approved
0.6566	Remote Similarity	NPD4138	Approved
0.6559	Remote Similarity	NPD6933	Approved
0.6557	Remote Similarity	NPD7319	Approved
0.6556	Remote Similarity	NPD4244	Approved
0.6556	Remote Similarity	NPD4245	Approved
0.6555	Remote Similarity	NPD7604	Phase 2
0.6552	Remote Similarity	NPD6313	Approved
0.6552	Remote Similarity	NPD6314	Approved
0.6545	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6909	Approved
0.6525	Remote Similarity	NPD5983	Phase 2
0.6525	Remote Similarity	NPD6908	Approved
0.6518	Remote Similarity	NPD5135	Approved
0.6518	Remote Similarity	NPD5249	Phase 3
0.6518	Remote Similarity	NPD5250	Approved
0.6518	Remote Similarity	NPD5169	Approved
0.6518	Remote Similarity	NPD5248	Approved
0.6518	Remote Similarity	NPD5247	Approved
0.6518	Remote Similarity	NPD5251	Approved
0.6518	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7492	Approved
0.6496	Remote Similarity	NPD7516	Approved
0.6484	Remote Similarity	NPD6081	Approved
0.6477	Remote Similarity	NPD4224	Phase 2
0.646	Remote Similarity	NPD5215	Approved
0.646	Remote Similarity	NPD5127	Approved
0.646	Remote Similarity	NPD5217	Approved
0.646	Remote Similarity	NPD5216	Approved
0.6458	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6336	Discontinued
0.6446	Remote Similarity	NPD6616	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