NPASS Compound

Structure

NPC78580 OpenBabel07101719252D 38 42 0 0 1 0 0 0 0 0999 V2000 -2.5377 4.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2062 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5144 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 3.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6918 0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5377 2.4419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7178 0.3575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0260 0.6192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2294 -0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8459 1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8459 -0.4884 0.0000 C 0 0 1 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 -2.5377 1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2294 4.3953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6945 0.3575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 1.2034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0028 0.6192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -0.2267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 5 30 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 29 1 0 0 0 0 13 31 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 17 30 1 0 0 0 0 18 21 1 0 0 0 0 18 28 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 0 0 0 0 21 27 1 6 0 0 0 22 29 1 1 0 0 0 22 31 1 0 0 0 0 23 29 1 1 0 0 0 23 32 1 0 0 0 0 24 32 1 6 0 0 0 24 38 1 0 0 0 0 25 28 1 0 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 26 32 1 0 0 0 0 26 36 2 0 0 0 0 26 37 1 0 0 0 0 27 2 1 1 0 0 0 28 3 1 1 0 0 0 29 4 1 1 0 0 0 30 31 1 1 0 0 0 31 6 1 1 0 0 0 32 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.35
Volume:	561.441
LogP:	4.862
LogD:	3.749
LogS:	-3.742
# Rotatable Bonds:	4
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	4.913
Fsp3:	0.844
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.556
MDCK Permeability:	6.0383081290638074e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	94.21375274658203%
Volume Distribution (VD):	0.629
Pgp-substrate:	3.8534395694732666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.363
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	1.285
Half-life (T1/2):	0.435

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.166
Skin Sensitization:	0.083
Carcinogencity:	0.08
Eye Corrosion:	0.76
Eye Irritation:	0.411
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC78580

Natural Product ID:	NPC78580
*Common Name:**	3Alpha-O-Acetylolean-12-En-23,29-Dioic Acid
IUPAC Name:	(2R,4aS,6aR,6aS,6bR,8aR,9S,10R,12aR,14bR)-10-acetyloxy-2,4a,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,9-dicarboxylic acid
Synonyms:
Standard InCHIKey:	UFBADNGLONOAHT-GEHWIPNRSA-N
Standard InCHI:	InChI=1S/C32H48O6/c1-19(33)38-24-11-12-29(4)22-9-8-20-21-18-28(3,25(34)35)15-14-27(21,2)16-17-30(20,5)31(22,6)13-10-23(29)32(24,7)26(36)37/h8,21-24H,9-18H2,1-7H3,(H,34,35)(H,36,37)/t21-,22+,23+,24+,27+,28+,29+,30+,31+,32-/m0/s1
SMILES:	CC(=O)O[C@@H]1CC[C@]2([C@H]([C@]1(C)C(=O)O)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2C[C@@](C)(CC1)C(=O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079031
PubChem CID:	44254604
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	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
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	150000.0	nM	PMID[572918]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	150000.0	nM	PMID[572918]

☑ 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 NPC78580 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	215
0.1-0.2	1349
0.2-0.3	4826
0.3-0.4	12238
0.4-0.5	10660
0.5-0.6	5631
0.6-0.7	4981
0.7-0.8	2058
0.8-0.85	423
0.85-0.9	163
0.9-0.95	122
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC23621
1.0	High Similarity	NPC184006
0.9886	High Similarity	NPC23241
0.9886	High Similarity	NPC195715
0.9667	High Similarity	NPC26413
0.9659	High Similarity	NPC86368
0.9655	High Similarity	NPC113989
0.9655	High Similarity	NPC120840
0.9545	High Similarity	NPC77099
0.9545	High Similarity	NPC155120
0.9545	High Similarity	NPC285184
0.9545	High Similarity	NPC60755
0.9545	High Similarity	NPC324341
0.9545	High Similarity	NPC966
0.9545	High Similarity	NPC470590
0.9545	High Similarity	NPC228784
0.9545	High Similarity	NPC282616
0.9545	High Similarity	NPC288833
0.954	High Similarity	NPC30522
0.9432	High Similarity	NPC86372
0.9432	High Similarity	NPC474728
0.9432	High Similarity	NPC172361
0.9348	High Similarity	NPC164349
0.9341	High Similarity	NPC98874
0.9333	High Similarity	NPC222047
0.9333	High Similarity	NPC296164
0.9333	High Similarity	NPC74751
0.9326	High Similarity	NPC6255
0.9326	High Similarity	NPC471588
0.9318	High Similarity	NPC61543
0.9318	High Similarity	NPC59263
0.9318	High Similarity	NPC225585
0.9318	High Similarity	NPC293048
0.9318	High Similarity	NPC127689
0.9318	High Similarity	NPC234346
0.9318	High Similarity	NPC121798
0.9318	High Similarity	NPC263393
0.9318	High Similarity	NPC130520
0.9318	High Similarity	NPC270768
0.931	High Similarity	NPC162107
0.931	High Similarity	NPC46912
0.9247	High Similarity	NPC475156
0.9247	High Similarity	NPC473576
0.9239	High Similarity	NPC476879
0.9239	High Similarity	NPC476878
0.9239	High Similarity	NPC158347
0.9231	High Similarity	NPC474727
0.9231	High Similarity	NPC148523
0.9222	High Similarity	NPC298554
0.9213	High Similarity	NPC130278
0.9213	High Similarity	NPC111110
0.9213	High Similarity	NPC126369
0.9213	High Similarity	NPC470589
0.9205	High Similarity	NPC246708
0.9205	High Similarity	NPC182797
0.9205	High Similarity	NPC40552
0.9205	High Similarity	NPC52169
0.9195	High Similarity	NPC10005
0.9195	High Similarity	NPC329943
0.9195	High Similarity	NPC9892
0.9195	High Similarity	NPC91525
0.9149	High Similarity	NPC93744
0.9149	High Similarity	NPC476888
0.913	High Similarity	NPC230151
0.913	High Similarity	NPC327179
0.913	High Similarity	NPC132824
0.913	High Similarity	NPC201657
0.9121	High Similarity	NPC209868
0.9121	High Similarity	NPC474529
0.9101	High Similarity	NPC474700
0.9101	High Similarity	NPC64872
0.9101	High Similarity	NPC198664
0.9101	High Similarity	NPC470588
0.9101	High Similarity	NPC274330
0.9101	High Similarity	NPC475049
0.9101	High Similarity	NPC25906
0.9101	High Similarity	NPC143232
0.9101	High Similarity	NPC290972
0.9091	High Similarity	NPC98442
0.9091	High Similarity	NPC293564
0.9091	High Similarity	NPC171203
0.9091	High Similarity	NPC307426
0.9091	High Similarity	NPC130577
0.9091	High Similarity	NPC88716
0.9091	High Similarity	NPC142415
0.9091	High Similarity	NPC18064
0.9091	High Similarity	NPC102683
0.9091	High Similarity	NPC68160
0.9091	High Similarity	NPC242468
0.9091	High Similarity	NPC51700
0.9053	High Similarity	NPC476890
0.9053	High Similarity	NPC40918
0.9032	High Similarity	NPC106112
0.9032	High Similarity	NPC261935
0.9011	High Similarity	NPC74855
0.9011	High Similarity	NPC63118
0.9011	High Similarity	NPC214756
0.9011	High Similarity	NPC136313
0.9011	High Similarity	NPC272075
0.9011	High Similarity	NPC307335
0.9011	High Similarity	NPC474436
0.9011	High Similarity	NPC295643
0.9011	High Similarity	NPC229281
0.9011	High Similarity	NPC49776
0.9	High Similarity	NPC210037
0.9	High Similarity	NPC273621
0.9	High Similarity	NPC290614
0.9	High Similarity	NPC227467
0.9	High Similarity	NPC18872
0.9	High Similarity	NPC120968
0.9	High Similarity	NPC477872
0.9	High Similarity	NPC7260
0.9	High Similarity	NPC291028
0.8989	High Similarity	NPC224145
0.8989	High Similarity	NPC290690
0.8989	High Similarity	NPC474512
0.8989	High Similarity	NPC470629
0.8989	High Similarity	NPC473242
0.8989	High Similarity	NPC181225
0.8989	High Similarity	NPC17733
0.8977	High Similarity	NPC325594
0.8977	High Similarity	NPC72638
0.8958	High Similarity	NPC476889
0.8936	High Similarity	NPC271614
0.8936	High Similarity	NPC29765
0.8936	High Similarity	NPC471966
0.8936	High Similarity	NPC111214
0.8936	High Similarity	NPC58942
0.8936	High Similarity	NPC260149
0.8936	High Similarity	NPC174663
0.8936	High Similarity	NPC188833
0.8925	High Similarity	NPC327788
0.8913	High Similarity	NPC20235
0.8913	High Similarity	NPC299996
0.8913	High Similarity	NPC159365
0.8913	High Similarity	NPC231063
0.8913	High Similarity	NPC282395
0.8913	High Similarity	NPC91010
0.8913	High Similarity	NPC6818
0.8913	High Similarity	NPC263548
0.8913	High Similarity	NPC32407
0.8913	High Similarity	NPC145667
0.8913	High Similarity	NPC191412
0.8913	High Similarity	NPC114159
0.8913	High Similarity	NPC88116
0.8901	High Similarity	NPC471901
0.8901	High Similarity	NPC65120
0.8901	High Similarity	NPC84319
0.8901	High Similarity	NPC306541
0.8901	High Similarity	NPC472149
0.8901	High Similarity	NPC235884
0.8901	High Similarity	NPC4036
0.8901	High Similarity	NPC474525
0.8901	High Similarity	NPC145067
0.8901	High Similarity	NPC158030
0.8901	High Similarity	NPC187722
0.8901	High Similarity	NPC71074
0.8901	High Similarity	NPC233455
0.8901	High Similarity	NPC25299
0.8901	High Similarity	NPC105189
0.8901	High Similarity	NPC475708
0.8901	High Similarity	NPC300351
0.8901	High Similarity	NPC52021
0.8889	High Similarity	NPC161751
0.8889	High Similarity	NPC474972
0.8889	High Similarity	NPC95246
0.8876	High Similarity	NPC158141
0.8876	High Similarity	NPC173089
0.8864	High Similarity	NPC191965
0.8851	High Similarity	NPC200752
0.8842	High Similarity	NPC35239
0.883	High Similarity	NPC89225
0.883	High Similarity	NPC187933
0.8804	High Similarity	NPC118519
0.8804	High Similarity	NPC202728
0.8804	High Similarity	NPC287118
0.8804	High Similarity	NPC275809
0.8804	High Similarity	NPC473690
0.8804	High Similarity	NPC118490
0.8804	High Similarity	NPC471902
0.8804	High Similarity	NPC169343
0.8804	High Similarity	NPC158059
0.8791	High Similarity	NPC49320
0.8791	High Similarity	NPC46441
0.8791	High Similarity	NPC193750
0.8791	High Similarity	NPC471896
0.8778	High Similarity	NPC474511
0.8778	High Similarity	NPC1753
0.8764	High Similarity	NPC73038
0.8764	High Similarity	NPC213412
0.8764	High Similarity	NPC84121
0.8764	High Similarity	NPC137306
0.875	High Similarity	NPC54909
0.875	High Similarity	NPC233012
0.8736	High Similarity	NPC286786
0.8723	High Similarity	NPC472806
0.8723	High Similarity	NPC167193
0.8723	High Similarity	NPC25848
0.8723	High Similarity	NPC73004
0.8723	High Similarity	NPC476318

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 NPC78580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1664
0.2-0.3	3806
0.3-0.4	2298
0.4-0.5	721
0.5-0.6	229
0.6-0.7	185
0.7-0.8	48
0.8-0.85	2
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD7748	Approved
0.9032	High Similarity	NPD7902	Approved
0.8901	High Similarity	NPD7515	Phase 2
0.871	High Similarity	NPD7901	Clinical (unspecified phase)
0.871	High Similarity	NPD7900	Approved
0.8298	Intermediate Similarity	NPD8034	Phase 2
0.8298	Intermediate Similarity	NPD8035	Phase 2
0.8182	Intermediate Similarity	NPD7645	Phase 2
0.8043	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD6399	Phase 3
0.7917	Intermediate Similarity	NPD6411	Approved
0.7789	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6101	Approved
0.7708	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD8328	Phase 3
0.7692	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD7128	Approved
0.7692	Intermediate Similarity	NPD5739	Approved
0.7636	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7638	Approved
0.7579	Intermediate Similarity	NPD7146	Approved
0.7579	Intermediate Similarity	NPD7334	Approved
0.7579	Intermediate Similarity	NPD5330	Approved
0.7579	Intermediate Similarity	NPD6409	Approved
0.7579	Intermediate Similarity	NPD7521	Approved
0.7579	Intermediate Similarity	NPD3618	Phase 1
0.7579	Intermediate Similarity	NPD6684	Approved
0.7553	Intermediate Similarity	NPD4786	Approved
0.7549	Intermediate Similarity	NPD7640	Approved
0.7549	Intermediate Similarity	NPD7639	Approved
0.7547	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD6881	Approved
0.7547	Intermediate Similarity	NPD7320	Approved
0.7527	Intermediate Similarity	NPD3667	Approved
0.7526	Intermediate Similarity	NPD5328	Approved
0.7526	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD6084	Phase 2
0.7525	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD3573	Approved
0.7477	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6372	Approved
0.7453	Intermediate Similarity	NPD5697	Approved
0.7453	Intermediate Similarity	NPD5701	Approved
0.7431	Intermediate Similarity	NPD8297	Approved
0.7423	Intermediate Similarity	NPD5737	Approved
0.7423	Intermediate Similarity	NPD6903	Approved
0.7423	Intermediate Similarity	NPD6672	Approved
0.7407	Intermediate Similarity	NPD7290	Approved
0.7407	Intermediate Similarity	NPD6883	Approved
0.7407	Intermediate Similarity	NPD7102	Approved
0.7374	Intermediate Similarity	NPD6079	Approved
0.7339	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD6617	Approved
0.7339	Intermediate Similarity	NPD6649	Approved
0.7339	Intermediate Similarity	NPD6847	Approved
0.7339	Intermediate Similarity	NPD6650	Approved
0.7327	Intermediate Similarity	NPD5695	Phase 3
0.7315	Intermediate Similarity	NPD6012	Approved
0.7315	Intermediate Similarity	NPD6014	Approved
0.7315	Intermediate Similarity	NPD6013	Approved
0.73	Intermediate Similarity	NPD5779	Approved
0.73	Intermediate Similarity	NPD5778	Approved
0.7282	Intermediate Similarity	NPD4225	Approved
0.7282	Intermediate Similarity	NPD5696	Approved
0.7273	Intermediate Similarity	NPD6882	Approved
0.7222	Intermediate Similarity	NPD6011	Approved
0.7216	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3133	Approved
0.7188	Intermediate Similarity	NPD3668	Phase 3
0.7188	Intermediate Similarity	NPD3665	Phase 1
0.7188	Intermediate Similarity	NPD3666	Approved
0.7184	Intermediate Similarity	NPD4755	Approved
0.7182	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7736	Approved
0.7129	Intermediate Similarity	NPD4202	Approved
0.7128	Intermediate Similarity	NPD7525	Registered
0.7087	Intermediate Similarity	NPD5222	Approved
0.7087	Intermediate Similarity	NPD4697	Phase 3
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.7087	Intermediate Similarity	NPD7732	Phase 3
0.7087	Intermediate Similarity	NPD5221	Approved
0.7087	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6117	Approved
0.7048	Intermediate Similarity	NPD5286	Approved
0.7048	Intermediate Similarity	NPD4700	Approved
0.7048	Intermediate Similarity	NPD4696	Approved
0.7048	Intermediate Similarity	NPD5285	Approved
0.7041	Intermediate Similarity	NPD6098	Approved
0.7019	Intermediate Similarity	NPD5173	Approved
0.7	Intermediate Similarity	NPD4753	Phase 2
0.7	Intermediate Similarity	NPD6904	Approved
0.7	Intermediate Similarity	NPD6673	Approved
0.7	Intermediate Similarity	NPD6080	Approved
0.6989	Remote Similarity	NPD6116	Phase 1
0.6983	Remote Similarity	NPD6319	Approved
0.6979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6412	Phase 2
0.6947	Remote Similarity	NPD4695	Discontinued
0.693	Remote Similarity	NPD6868	Approved
0.693	Remote Similarity	NPD6274	Approved
0.6917	Remote Similarity	NPD8293	Discontinued
0.6916	Remote Similarity	NPD7632	Discontinued
0.6916	Remote Similarity	NPD5211	Phase 2
0.6916	Remote Similarity	NPD5224	Approved
0.6916	Remote Similarity	NPD5225	Approved
0.6916	Remote Similarity	NPD5226	Approved
0.6916	Remote Similarity	NPD4633	Approved
0.6915	Remote Similarity	NPD6115	Approved
0.6915	Remote Similarity	NPD6118	Approved
0.6915	Remote Similarity	NPD6114	Approved
0.6915	Remote Similarity	NPD6697	Approved
0.6909	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8133	Approved
0.6897	Remote Similarity	NPD7100	Approved
0.6897	Remote Similarity	NPD7101	Approved
0.6891	Remote Similarity	NPD7492	Approved
0.6881	Remote Similarity	NPD6008	Approved
0.6863	Remote Similarity	NPD7637	Suspended
0.6852	Remote Similarity	NPD5175	Approved
0.6852	Remote Similarity	NPD5174	Approved
0.6848	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6059	Approved
0.6838	Remote Similarity	NPD6054	Approved
0.6833	Remote Similarity	NPD6616	Approved
0.6822	Remote Similarity	NPD5223	Approved
0.681	Remote Similarity	NPD6335	Approved
0.6804	Remote Similarity	NPD4221	Approved
0.6804	Remote Similarity	NPD4223	Phase 3
0.6803	Remote Similarity	NPD7319	Approved
0.6789	Remote Similarity	NPD5141	Approved
0.6786	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4634	Approved
0.678	Remote Similarity	NPD6909	Approved
0.678	Remote Similarity	NPD6908	Approved
0.6777	Remote Similarity	NPD7078	Approved
0.6774	Remote Similarity	NPD6942	Approved
0.6774	Remote Similarity	NPD7339	Approved
0.6768	Remote Similarity	NPD5329	Approved
0.6768	Remote Similarity	NPD1694	Approved
0.6757	Remote Similarity	NPD6686	Approved
0.6754	Remote Similarity	NPD4632	Approved
0.6733	Remote Similarity	NPD5208	Approved
0.6731	Remote Similarity	NPD6001	Approved
0.6727	Remote Similarity	NPD4767	Approved
0.6727	Remote Similarity	NPD4768	Approved
0.6724	Remote Similarity	NPD6317	Approved
0.6723	Remote Similarity	NPD6370	Approved
0.6702	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5279	Phase 3
0.6699	Remote Similarity	NPD5281	Approved
0.6699	Remote Similarity	NPD6050	Approved
0.6699	Remote Similarity	NPD5284	Approved
0.6699	Remote Similarity	NPD5693	Phase 1
0.6697	Remote Similarity	NPD4754	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6639	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD6016	Approved
0.6607	Remote Similarity	NPD4730	Approved
0.6607	Remote Similarity	NPD5128	Approved
0.6607	Remote Similarity	NPD4729	Approved
0.6602	Remote Similarity	NPD5692	Phase 3
0.6596	Remote Similarity	NPD8039	Approved
0.6583	Remote Similarity	NPD5988	Approved
0.6581	Remote Similarity	NPD6009	Approved
0.6566	Remote Similarity	NPD4788	Approved
0.6562	Remote Similarity	NPD3617	Approved
0.6555	Remote Similarity	NPD8294	Approved
0.6555	Remote Similarity	NPD8377	Approved
0.6538	Remote Similarity	NPD5694	Approved
0.6535	Remote Similarity	NPD5205	Approved
0.6535	Remote Similarity	NPD4690	Approved
0.6535	Remote Similarity	NPD4519	Discontinued
0.6535	Remote Similarity	NPD4623	Approved
0.6535	Remote Similarity	NPD4138	Approved
0.6535	Remote Similarity	NPD4689	Approved
0.6535	Remote Similarity	NPD4693	Phase 3
0.6535	Remote Similarity	NPD4688	Approved
0.6531	Remote Similarity	NPD5369	Approved
0.6529	Remote Similarity	NPD7604	Phase 2
0.6518	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8380	Approved
0.65	Remote Similarity	NPD8379	Approved
0.65	Remote Similarity	NPD8378	Approved
0.65	Remote Similarity	NPD8513	Phase 3
0.65	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD8515	Approved
0.65	Remote Similarity	NPD8033	Approved
0.65	Remote Similarity	NPD8517	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