NPASS Compound

Structure

NPC118490 OpenBabel07101718192D 35 39 0 0 1 0 0 0 0 0999 V2000 -3.5324 -4.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1227 -3.7856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3319 2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0662 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3775 -2.9250 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0662 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3569 2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3775 -1.9500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9106 -3.4125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 3.1512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6181 2.3069 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 19 1 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 17 30 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 27 1 1 0 0 0 20 24 1 0 0 0 0 20 27 1 1 0 0 0 21 24 1 0 0 0 0 21 31 2 0 0 0 0 22 29 1 1 0 0 0 22 32 1 0 0 0 0 23 25 1 0 0 0 0 23 33 2 0 0 0 0 23 34 1 0 0 0 0 25 3 1 1 0 0 0 26 30 1 1 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 30 1 1 0 0 0 30 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	520.695
LogP:	3.525
LogD:	2.872
LogS:	-4.185
# Rotatable Bonds:	1
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.424
Synthetic Accessibility Score:	5.293
Fsp3:	0.867
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:	-5.383
MDCK Permeability:	2.1518610083148815e-05
Pgp-inhibitor:	0.248
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.749
30% Bioavailability (F30%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	91.580810546875%
Volume Distribution (VD):	0.654
Pgp-substrate:	4.367434024810791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.885
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.84
CYP2C9-inhibitor:	0.122
CYP2C9-substrate:	0.652
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.419
CYP3A4-substrate:	0.346

ADMET: Excretion

Clearance (CL):	1.819
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.727
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.38
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.034
Carcinogencity:	0.578
Eye Corrosion:	0.008
Eye Irritation:	0.026
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC118490

Natural Product ID:	NPC118490
*Common Name:**	Sandorinic Acid B
IUPAC Name:	(2R,4aS,6aR,6aR,8aR,12aR,14R,14aS,14bS)-14,14b-dihydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-1,3,4,5,6,6a,8,8a,11,12,13,14-dodecahydropicene-2-carboxylic acid
Synonyms:	Sandorinic acid B
Standard InCHIKey:	ZOJYWIDATCZFTE-GLLUEPBVSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-24(2)20-9-8-18-19(27(20,5)11-10-21(24)31)16-22(32)29(7)28(18,6)15-14-26(4)13-12-25(3,23(33)34)17-30(26,29)35/h8,19-20,22,32,35H,9-17H2,1-7H3,(H,33,34)/t19-,20-,22+,25+,26+,27+,28+,29+,30-/m0/s1
SMILES:	CC1(C)[C@@H]2CC=C3[C@H](C[C@H]([C@]4(C)[C@]3(C)CC[C@@]3(C)CC[C@](C)(C[C@@]43O)C(=O)O)O)[C@@]2(C)CCC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465066
PubChem CID:	10323148
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
NPO26165	Sandoricum indicum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575968]
NPO26165	Sandoricum indicum	Species	Meliaceae	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	6

Activity Type	# Activity
Cell Line	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	16.0	ug.mL-1	PMID[485632]
NPT168	Cell Line	P388	Mus musculus	IC50	=	18.0	ug.mL-1	PMID[485632]
NPT2831	Cell Line	P388/S	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[485632]
NPT168	Cell Line	P388	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[485632]
NPT2	Others	Unspecified		IC50	=	50.0	ug.mL-1	PMID[485632]

☑ 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 NPC118490 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	213
0.1-0.2	1393
0.2-0.3	5096
0.3-0.4	13578
0.4-0.5	8790
0.5-0.6	5808
0.6-0.7	4979
0.7-0.8	2324
0.8-0.85	194
0.85-0.9	138
0.9-0.95	159
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC193750
0.9659	High Similarity	NPC6818
0.9659	High Similarity	NPC114159
0.9659	High Similarity	NPC191412
0.9655	High Similarity	NPC105189
0.9655	High Similarity	NPC38754
0.9545	High Similarity	NPC229281
0.9545	High Similarity	NPC118519
0.9545	High Similarity	NPC202728
0.9545	High Similarity	NPC158059
0.954	High Similarity	NPC291028
0.954	High Similarity	NPC210037
0.954	High Similarity	NPC290614
0.954	High Similarity	NPC130278
0.954	High Similarity	NPC7260
0.954	High Similarity	NPC120968
0.954	High Similarity	NPC227467
0.954	High Similarity	NPC477872
0.954	High Similarity	NPC18872
0.954	High Similarity	NPC273621
0.9444	High Similarity	NPC157113
0.9444	High Similarity	NPC62516
0.9444	High Similarity	NPC132824
0.9444	High Similarity	NPC116457
0.9438	High Similarity	NPC148964
0.9432	High Similarity	NPC471588
0.9432	High Similarity	NPC6255
0.9432	High Similarity	NPC187722
0.9425	High Similarity	NPC127689
0.9425	High Similarity	NPC293048
0.9425	High Similarity	NPC130520
0.9425	High Similarity	NPC25906
0.9425	High Similarity	NPC234346
0.9425	High Similarity	NPC290972
0.9425	High Similarity	NPC64872
0.9425	High Similarity	NPC121798
0.9425	High Similarity	NPC61543
0.9425	High Similarity	NPC263393
0.9425	High Similarity	NPC270768
0.9425	High Similarity	NPC225585
0.9425	High Similarity	NPC59263
0.9341	High Similarity	NPC247139
0.9341	High Similarity	NPC9613
0.9333	High Similarity	NPC83693
0.9318	High Similarity	NPC126369
0.9318	High Similarity	NPC470589
0.9318	High Similarity	NPC111110
0.931	High Similarity	NPC182797
0.931	High Similarity	NPC52169
0.9247	High Similarity	NPC118964
0.9239	High Similarity	NPC174663
0.9231	High Similarity	NPC259733
0.9231	High Similarity	NPC327179
0.9231	High Similarity	NPC158371
0.9231	High Similarity	NPC173744
0.9231	High Similarity	NPC207922
0.9231	High Similarity	NPC73004
0.9231	High Similarity	NPC204961
0.9222	High Similarity	NPC60692
0.9222	High Similarity	NPC263548
0.9222	High Similarity	NPC32407
0.9222	High Similarity	NPC299996
0.9222	High Similarity	NPC20235
0.9222	High Similarity	NPC231063
0.9222	High Similarity	NPC145667
0.9222	High Similarity	NPC88116
0.9222	High Similarity	NPC282395
0.9213	High Similarity	NPC324341
0.9213	High Similarity	NPC966
0.9213	High Similarity	NPC235704
0.9213	High Similarity	NPC145067
0.9213	High Similarity	NPC233455
0.9213	High Similarity	NPC155120
0.9213	High Similarity	NPC282616
0.9213	High Similarity	NPC288833
0.9213	High Similarity	NPC158030
0.9213	High Similarity	NPC4036
0.9213	High Similarity	NPC65120
0.9213	High Similarity	NPC474525
0.9213	High Similarity	NPC228784
0.9205	High Similarity	NPC198664
0.9205	High Similarity	NPC274330
0.9205	High Similarity	NPC143232
0.9195	High Similarity	NPC130577
0.9195	High Similarity	NPC98442
0.9195	High Similarity	NPC293564
0.9195	High Similarity	NPC242468
0.9195	High Similarity	NPC171203
0.9195	High Similarity	NPC68160
0.9195	High Similarity	NPC307426
0.9195	High Similarity	NPC102683
0.9195	High Similarity	NPC88716
0.9195	High Similarity	NPC142415
0.9195	High Similarity	NPC51700
0.9195	High Similarity	NPC18064
0.914	High Similarity	NPC35239
0.913	High Similarity	NPC255589
0.913	High Similarity	NPC106112
0.913	High Similarity	NPC259788
0.913	High Similarity	NPC261935
0.913	High Similarity	NPC187933
0.9121	High Similarity	NPC139570
0.9121	High Similarity	NPC290481
0.9121	High Similarity	NPC96916
0.9121	High Similarity	NPC148523
0.9111	High Similarity	NPC214756
0.9111	High Similarity	NPC275809
0.9111	High Similarity	NPC272075
0.9111	High Similarity	NPC295643
0.9111	High Similarity	NPC86368
0.9101	High Similarity	NPC46441
0.9101	High Similarity	NPC86372
0.9101	High Similarity	NPC172361
0.9091	High Similarity	NPC17733
0.9091	High Similarity	NPC40552
0.9091	High Similarity	NPC474512
0.9091	High Similarity	NPC470629
0.9091	High Similarity	NPC290690
0.9091	High Similarity	NPC181225
0.9091	High Similarity	NPC473242
0.9091	High Similarity	NPC246708
0.908	High Similarity	NPC213412
0.908	High Similarity	NPC74363
0.908	High Similarity	NPC72638
0.908	High Similarity	NPC475862
0.9043	High Similarity	NPC256247
0.9032	High Similarity	NPC111214
0.9032	High Similarity	NPC271614
0.9032	High Similarity	NPC29765
0.9032	High Similarity	NPC164349
0.9022	High Similarity	NPC25848
0.9022	High Similarity	NPC201657
0.9022	High Similarity	NPC98874
0.9022	High Similarity	NPC305464
0.9022	High Similarity	NPC307282
0.9022	High Similarity	NPC19376
0.9022	High Similarity	NPC476327
0.9022	High Similarity	NPC476318
0.9011	High Similarity	NPC222047
0.9011	High Similarity	NPC159365
0.9011	High Similarity	NPC474529
0.9	High Similarity	NPC84319
0.9	High Similarity	NPC52021
0.9	High Similarity	NPC306541
0.9	High Similarity	NPC25299
0.9	High Similarity	NPC300351
0.9	High Similarity	NPC71074
0.9	High Similarity	NPC235884
0.9	High Similarity	NPC472149
0.9	High Similarity	NPC475708
0.8989	High Similarity	NPC470588
0.8989	High Similarity	NPC161751
0.8989	High Similarity	NPC95246
0.8989	High Similarity	NPC474972
0.8989	High Similarity	NPC281524
0.8977	High Similarity	NPC73064
0.8977	High Similarity	NPC173089
0.8977	High Similarity	NPC158141
0.8966	High Similarity	NPC133954
0.8925	High Similarity	NPC203343
0.8925	High Similarity	NPC312075
0.8925	High Similarity	NPC43686
0.8913	High Similarity	NPC473240
0.8913	High Similarity	NPC32118
0.8901	High Similarity	NPC298554
0.8901	High Similarity	NPC136313
0.8901	High Similarity	NPC474436
0.8901	High Similarity	NPC307335
0.8901	High Similarity	NPC74855
0.8901	High Similarity	NPC49776
0.8901	High Similarity	NPC63118
0.8889	High Similarity	NPC474728
0.8889	High Similarity	NPC120840
0.8889	High Similarity	NPC49320
0.8889	High Similarity	NPC113989
0.8876	High Similarity	NPC474511
0.8876	High Similarity	NPC1753
0.8864	High Similarity	NPC73038
0.8842	High Similarity	NPC233012
0.8842	High Similarity	NPC54909
0.883	High Similarity	NPC471966
0.8817	High Similarity	NPC472806
0.8817	High Similarity	NPC167193
0.8804	High Similarity	NPC80365
0.8804	High Similarity	NPC184006
0.8804	High Similarity	NPC209868
0.8804	High Similarity	NPC78580
0.8804	High Similarity	NPC74751
0.8804	High Similarity	NPC91010
0.8804	High Similarity	NPC23621
0.8791	High Similarity	NPC470590
0.8791	High Similarity	NPC60755
0.8791	High Similarity	NPC285184
0.8791	High Similarity	NPC77099
0.8778	High Similarity	NPC474686
0.8778	High Similarity	NPC30522
0.8764	High Similarity	NPC71507
0.8763	High Similarity	NPC284865
0.8723	High Similarity	NPC476879
0.8723	High Similarity	NPC89225

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 NPC118490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1749
0.2-0.3	3841
0.3-0.4	2234
0.4-0.5	675
0.5-0.6	195
0.6-0.7	176
0.7-0.8	84
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9213	High Similarity	NPD7515	Phase 2
0.8925	High Similarity	NPD7902	Approved
0.8804	High Similarity	NPD7748	Approved
0.8602	High Similarity	NPD7900	Approved
0.8602	High Similarity	NPD7901	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6399	Phase 3
0.8068	Intermediate Similarity	NPD7645	Phase 2
0.8043	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD8034	Phase 2
0.8	Intermediate Similarity	NPD8035	Phase 2
0.7941	Intermediate Similarity	NPD6675	Approved
0.7941	Intermediate Similarity	NPD6402	Approved
0.7941	Intermediate Similarity	NPD7128	Approved
0.7941	Intermediate Similarity	NPD5739	Approved
0.7885	Intermediate Similarity	NPD6372	Approved
0.7885	Intermediate Similarity	NPD6373	Approved
0.7826	Intermediate Similarity	NPD4786	Approved
0.7802	Intermediate Similarity	NPD3667	Approved
0.7789	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5328	Approved
0.7788	Intermediate Similarity	NPD6899	Approved
0.7788	Intermediate Similarity	NPD6881	Approved
0.7788	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD6083	Phase 2
0.7778	Intermediate Similarity	NPD6084	Phase 2
0.7778	Intermediate Similarity	NPD4755	Approved
0.7736	Intermediate Similarity	NPD6649	Approved
0.7736	Intermediate Similarity	NPD6650	Approved
0.7732	Intermediate Similarity	NPD4202	Approved
0.7692	Intermediate Similarity	NPD5697	Approved
0.7692	Intermediate Similarity	NPD5701	Approved
0.7684	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7290	Approved
0.7642	Intermediate Similarity	NPD6883	Approved
0.7642	Intermediate Similarity	NPD7102	Approved
0.7634	Intermediate Similarity	NPD3665	Phase 1
0.7634	Intermediate Similarity	NPD3133	Approved
0.7634	Intermediate Similarity	NPD3666	Approved
0.7629	Intermediate Similarity	NPD6079	Approved
0.7624	Intermediate Similarity	NPD4700	Approved
0.7624	Intermediate Similarity	NPD5286	Approved
0.7624	Intermediate Similarity	NPD4696	Approved
0.7624	Intermediate Similarity	NPD5285	Approved
0.7604	Intermediate Similarity	NPD4753	Phase 2
0.7582	Intermediate Similarity	NPD7525	Registered
0.757	Intermediate Similarity	NPD6847	Approved
0.757	Intermediate Similarity	NPD6617	Approved
0.757	Intermediate Similarity	NPD8130	Phase 1
0.757	Intermediate Similarity	NPD6869	Approved
0.7547	Intermediate Similarity	NPD6014	Approved
0.7547	Intermediate Similarity	NPD6012	Approved
0.7547	Intermediate Similarity	NPD6013	Approved
0.7547	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5696	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.7476	Intermediate Similarity	NPD5226	Approved
0.7476	Intermediate Similarity	NPD5224	Approved
0.7476	Intermediate Similarity	NPD4633	Approved
0.7476	Intermediate Similarity	NPD5211	Phase 2
0.7476	Intermediate Similarity	NPD5225	Approved
0.7474	Intermediate Similarity	NPD7146	Approved
0.7474	Intermediate Similarity	NPD7521	Approved
0.7474	Intermediate Similarity	NPD7334	Approved
0.7474	Intermediate Similarity	NPD6409	Approved
0.7474	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6684	Approved
0.7474	Intermediate Similarity	NPD5330	Approved
0.7456	Intermediate Similarity	NPD8328	Phase 3
0.7453	Intermediate Similarity	NPD6011	Approved
0.7449	Intermediate Similarity	NPD5281	Approved
0.7449	Intermediate Similarity	NPD5284	Approved
0.7449	Intermediate Similarity	NPD6411	Approved
0.7407	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5175	Approved
0.7404	Intermediate Similarity	NPD5174	Approved
0.74	Intermediate Similarity	NPD4629	Approved
0.74	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5695	Phase 3
0.74	Intermediate Similarity	NPD5210	Approved
0.7396	Intermediate Similarity	NPD3573	Approved
0.7387	Intermediate Similarity	NPD7115	Discovery
0.7379	Intermediate Similarity	NPD5223	Approved
0.7353	Intermediate Similarity	NPD7638	Approved
0.7333	Intermediate Similarity	NPD5141	Approved
0.7327	Intermediate Similarity	NPD5222	Approved
0.7327	Intermediate Similarity	NPD5221	Approved
0.7327	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7614	Phase 1
0.732	Intermediate Similarity	NPD6672	Approved
0.732	Intermediate Similarity	NPD5737	Approved
0.732	Intermediate Similarity	NPD6903	Approved
0.7282	Intermediate Similarity	NPD7639	Approved
0.7282	Intermediate Similarity	NPD7640	Approved
0.7264	Intermediate Similarity	NPD4768	Approved
0.7264	Intermediate Similarity	NPD4767	Approved
0.7263	Intermediate Similarity	NPD3668	Phase 3
0.7255	Intermediate Similarity	NPD5173	Approved
0.7253	Intermediate Similarity	NPD6116	Phase 1
0.7245	Intermediate Similarity	NPD6101	Approved
0.7245	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4754	Approved
0.7234	Intermediate Similarity	NPD4221	Approved
0.7234	Intermediate Similarity	NPD4223	Phase 3
0.7232	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4695	Discontinued
0.7196	Intermediate Similarity	NPD6412	Phase 2
0.7188	Intermediate Similarity	NPD5329	Approved
0.7158	Intermediate Similarity	NPD4788	Approved
0.7143	Intermediate Similarity	NPD6274	Approved
0.7143	Intermediate Similarity	NPD6117	Approved
0.713	Intermediate Similarity	NPD5128	Approved
0.713	Intermediate Similarity	NPD4730	Approved
0.713	Intermediate Similarity	NPD4729	Approved
0.7117	Intermediate Similarity	NPD4632	Approved
0.7113	Intermediate Similarity	NPD5279	Phase 3
0.7113	Intermediate Similarity	NPD6098	Approved
0.7105	Intermediate Similarity	NPD7100	Approved
0.7105	Intermediate Similarity	NPD7101	Approved
0.7103	Intermediate Similarity	NPD6008	Approved
0.7083	Intermediate Similarity	NPD4197	Approved
0.7071	Intermediate Similarity	NPD6904	Approved
0.7071	Intermediate Similarity	NPD6673	Approved
0.7071	Intermediate Similarity	NPD6080	Approved
0.7018	Intermediate Similarity	NPD6335	Approved
0.7	Intermediate Similarity	NPD5250	Approved
0.7	Intermediate Similarity	NPD5248	Approved
0.7	Intermediate Similarity	NPD5249	Phase 3
0.7	Intermediate Similarity	NPD4634	Approved
0.7	Intermediate Similarity	NPD5251	Approved
0.7	Intermediate Similarity	NPD5247	Approved
0.699	Remote Similarity	NPD7732	Phase 3
0.6989	Remote Similarity	NPD6115	Approved
0.6989	Remote Similarity	NPD6114	Approved
0.6989	Remote Similarity	NPD6118	Approved
0.6989	Remote Similarity	NPD6697	Approved
0.6983	Remote Similarity	NPD6908	Approved
0.6983	Remote Similarity	NPD6909	Approved
0.6972	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6001	Approved
0.6939	Remote Similarity	NPD4138	Approved
0.6939	Remote Similarity	NPD4693	Phase 3
0.6939	Remote Similarity	NPD5205	Approved
0.6939	Remote Similarity	NPD4623	Approved
0.6939	Remote Similarity	NPD4689	Approved
0.6939	Remote Similarity	NPD4688	Approved
0.6939	Remote Similarity	NPD4519	Discontinued
0.6939	Remote Similarity	NPD4690	Approved
0.6937	Remote Similarity	NPD5215	Approved
0.6937	Remote Similarity	NPD5216	Approved
0.6937	Remote Similarity	NPD5217	Approved
0.693	Remote Similarity	NPD6009	Approved
0.693	Remote Similarity	NPD6317	Approved
0.6923	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7736	Approved
0.6909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6319	Approved
0.687	Remote Similarity	NPD6313	Approved
0.687	Remote Similarity	NPD6314	Approved
0.6863	Remote Similarity	NPD5779	Approved
0.6863	Remote Similarity	NPD5778	Approved
0.6857	Remote Similarity	NPD4225	Approved
0.6848	Remote Similarity	NPD7339	Approved
0.6848	Remote Similarity	NPD6942	Approved
0.6847	Remote Similarity	NPD5135	Approved
0.6847	Remote Similarity	NPD5169	Approved
0.6847	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5368	Approved
0.6842	Remote Similarity	NPD6868	Approved
0.6838	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD1694	Approved
0.6818	Remote Similarity	NPD6686	Approved
0.6814	Remote Similarity	NPD8133	Approved
0.6809	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3617	Approved
0.6807	Remote Similarity	NPD7492	Approved
0.68	Remote Similarity	NPD5208	Approved
0.6786	Remote Similarity	NPD5127	Approved
0.6774	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5369	Approved
0.6768	Remote Similarity	NPD5280	Approved
0.6768	Remote Similarity	NPD4694	Approved
0.6768	Remote Similarity	NPD5690	Phase 2
0.6765	Remote Similarity	NPD6050	Approved
0.6765	Remote Similarity	NPD5693	Phase 1
0.6752	Remote Similarity	NPD6059	Approved
0.6752	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6616	Approved
0.675	Remote Similarity	NPD7507	Approved
0.6723	Remote Similarity	NPD7604	Phase 2
0.6703	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6435	Approved
0.6701	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5983	Phase 2
0.6694	Remote Similarity	NPD7078	Approved
0.6694	Remote Similarity	NPD8293	Discontinued

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