NPASS Compound

Structure

NPC235704 OpenBabel07101718302D 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 0 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 1 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 2 0 0 0 0 18 28 1 0 0 0 0 19 27 1 0 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:	3.341
LogD:	2.312
LogS:	-4.142
# 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:	0.415
Synthetic Accessibility Score:	5.257
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:	-5.499
MDCK Permeability:	1.3996023881190922e-05
Pgp-inhibitor:	0.154
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.303
Plasma Protein Binding (PPB):	89.47027587890625%
Volume Distribution (VD):	0.729
Pgp-substrate:	4.27083683013916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.891
CYP2C9-inhibitor:	0.1
CYP2C9-substrate:	0.488
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.376
CYP3A4-substrate:	0.763

ADMET: Excretion

Clearance (CL):	1.884
Half-life (T1/2):	0.351

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.704
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.891
Skin Sensitization:	0.025
Carcinogencity:	0.946
Eye Corrosion:	0.005
Eye Irritation:	0.014
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC235704

Natural Product ID:	NPC235704
*Common Name:**	Sandorinic Acid A
IUPAC Name:	(2R,4aS,6aR,8aR,12aS,14R,14aS,14bS)-14,14b-dihydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-10-oxo-1,3,4,5,6,7,8,8a,11,12,13,14-dodecahydropicene-2-carboxylic acid
Synonyms:
Standard InCHIKey:	PLEQWDWYBBEGIT-ZTSHXWEVSA-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/h20,22,32,35H,8-17H2,1-7H3,(H,33,34)/t20-,22+,25+,26+,27+,28+,29+,30-/m0/s1
SMILES:	CC1(C)[C@@H]2CCC3=C(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:	CHEMBL464226
PubChem CID:	10323147
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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	7

Activity Type	# Activity
Cell Line	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	9.0	ug.mL-1	PMID[450167]
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[450167]
NPT2831	Cell Line	P388/S	Mus musculus	IC50	=	16.0	ug.mL-1	PMID[450167]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	15.0	ug.mL-1	PMID[450167]
NPT2	Others	Unspecified		IC50	=	25.0	ug.mL-1	PMID[450167]

☑ 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 NPC235704 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	234
0.1-0.2	1600
0.2-0.3	5538
0.3-0.4	14301
0.4-0.5	7944
0.5-0.6	5761
0.6-0.7	5126
0.7-0.8	1832
0.8-0.85	270
0.85-0.9	81
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC56588
0.9326	High Similarity	NPC114159
0.9326	High Similarity	NPC191412
0.9326	High Similarity	NPC6818
0.9213	High Similarity	NPC158059
0.9213	High Similarity	NPC229281
0.9213	High Similarity	NPC118519
0.9213	High Similarity	NPC202728
0.9213	High Similarity	NPC118490
0.9176	High Similarity	NPC171789
0.9121	High Similarity	NPC116457
0.9121	High Similarity	NPC157113
0.9121	High Similarity	NPC62516
0.9121	High Similarity	NPC132824
0.9101	High Similarity	NPC187722
0.9101	High Similarity	NPC38754
0.9101	High Similarity	NPC105189
0.9022	High Similarity	NPC9613
0.9022	High Similarity	NPC247139
0.9011	High Similarity	NPC32118
0.8989	High Similarity	NPC130278
0.8989	High Similarity	NPC210037
0.8989	High Similarity	NPC273621
0.8989	High Similarity	NPC477872
0.8989	High Similarity	NPC7260
0.8989	High Similarity	NPC111110
0.8989	High Similarity	NPC193750
0.8989	High Similarity	NPC126369
0.8989	High Similarity	NPC120968
0.8989	High Similarity	NPC18872
0.8989	High Similarity	NPC290614
0.8989	High Similarity	NPC291028
0.8989	High Similarity	NPC227467
0.8989	High Similarity	NPC470589
0.8936	High Similarity	NPC118964
0.8925	High Similarity	NPC174663
0.8913	High Similarity	NPC158371
0.8913	High Similarity	NPC259733
0.8913	High Similarity	NPC327179
0.8913	High Similarity	NPC173744
0.8913	High Similarity	NPC73004
0.8913	High Similarity	NPC204961
0.8913	High Similarity	NPC207922
0.8913	High Similarity	NPC88847
0.8901	High Similarity	NPC80365
0.8901	High Similarity	NPC148964
0.8876	High Similarity	NPC25906
0.8876	High Similarity	NPC61543
0.8876	High Similarity	NPC143232
0.8876	High Similarity	NPC234346
0.8876	High Similarity	NPC64872
0.8876	High Similarity	NPC225585
0.8876	High Similarity	NPC263393
0.8876	High Similarity	NPC198664
0.8876	High Similarity	NPC270768
0.8876	High Similarity	NPC274330
0.8876	High Similarity	NPC121798
0.8876	High Similarity	NPC293048
0.8876	High Similarity	NPC127689
0.8876	High Similarity	NPC290972
0.8876	High Similarity	NPC59263
0.8876	High Similarity	NPC130520
0.8864	High Similarity	NPC71507
0.883	High Similarity	NPC35239
0.8817	High Similarity	NPC255589
0.8817	High Similarity	NPC259788
0.8817	High Similarity	NPC187933
0.8804	High Similarity	NPC96916
0.8804	High Similarity	NPC83693
0.8791	High Similarity	NPC474806
0.8791	High Similarity	NPC133579
0.8764	High Similarity	NPC474512
0.8764	High Similarity	NPC470629
0.8764	High Similarity	NPC182797
0.8764	High Similarity	NPC52169
0.8764	High Similarity	NPC473242
0.8764	High Similarity	NPC181225
0.8764	High Similarity	NPC17733
0.8764	High Similarity	NPC290690
0.875	High Similarity	NPC72638
0.8737	High Similarity	NPC256247
0.8723	High Similarity	NPC29765
0.8723	High Similarity	NPC271614
0.8723	High Similarity	NPC111214
0.871	High Similarity	NPC476327
0.871	High Similarity	NPC476318
0.8696	High Similarity	NPC159365
0.8696	High Similarity	NPC88116
0.8696	High Similarity	NPC231063
0.8696	High Similarity	NPC145667
0.8696	High Similarity	NPC282395
0.8696	High Similarity	NPC299996
0.8696	High Similarity	NPC32407
0.8696	High Similarity	NPC263548
0.8696	High Similarity	NPC20235
0.8696	High Similarity	NPC60692
0.8681	High Similarity	NPC158030
0.8681	High Similarity	NPC65120
0.8681	High Similarity	NPC228784
0.8681	High Similarity	NPC282616
0.8681	High Similarity	NPC474525
0.8681	High Similarity	NPC155120
0.8681	High Similarity	NPC324341
0.8681	High Similarity	NPC301244
0.8681	High Similarity	NPC288833
0.8681	High Similarity	NPC4036
0.8681	High Similarity	NPC966
0.8681	High Similarity	NPC471588
0.8681	High Similarity	NPC145067
0.8681	High Similarity	NPC6255
0.8681	High Similarity	NPC233455
0.8681	High Similarity	NPC475708
0.8667	High Similarity	NPC470588
0.8667	High Similarity	NPC474686
0.8652	High Similarity	NPC102683
0.8652	High Similarity	NPC130577
0.8652	High Similarity	NPC18064
0.8652	High Similarity	NPC88716
0.8652	High Similarity	NPC98442
0.8652	High Similarity	NPC171203
0.8652	High Similarity	NPC142415
0.8652	High Similarity	NPC68160
0.8652	High Similarity	NPC73064
0.8652	High Similarity	NPC293564
0.8652	High Similarity	NPC51700
0.8652	High Similarity	NPC307426
0.8652	High Similarity	NPC242468
0.8617	High Similarity	NPC43686
0.8617	High Similarity	NPC261935
0.8617	High Similarity	NPC106112
0.8602	High Similarity	NPC290481
0.8602	High Similarity	NPC148523
0.8602	High Similarity	NPC139570
0.8602	High Similarity	NPC473240
0.8587	High Similarity	NPC295643
0.8587	High Similarity	NPC275809
0.8587	High Similarity	NPC272075
0.8587	High Similarity	NPC86368
0.8587	High Similarity	NPC214756
0.8571	High Similarity	NPC46441
0.8571	High Similarity	NPC86372
0.8571	High Similarity	NPC172361
0.8571	High Similarity	NPC49320
0.8571	High Similarity	NPC474728
0.8556	High Similarity	NPC40552
0.8556	High Similarity	NPC230387
0.8556	High Similarity	NPC246708
0.8542	High Similarity	NPC54909
0.8542	High Similarity	NPC233012
0.8539	High Similarity	NPC73038
0.8539	High Similarity	NPC213412
0.8539	High Similarity	NPC475862
0.8539	High Similarity	NPC74363
0.8526	High Similarity	NPC164349
0.8511	High Similarity	NPC19376
0.8511	High Similarity	NPC201657
0.8511	High Similarity	NPC167193
0.8511	High Similarity	NPC98874
0.8511	High Similarity	NPC25848
0.8511	High Similarity	NPC307282
0.8511	High Similarity	NPC305464
0.8511	High Similarity	NPC472806
0.8495	Intermediate Similarity	NPC474529
0.8495	Intermediate Similarity	NPC209868
0.8495	Intermediate Similarity	NPC222047
0.8478	Intermediate Similarity	NPC306541
0.8478	Intermediate Similarity	NPC60755
0.8478	Intermediate Similarity	NPC472149
0.8478	Intermediate Similarity	NPC285184
0.8478	Intermediate Similarity	NPC235884
0.8478	Intermediate Similarity	NPC84319
0.8478	Intermediate Similarity	NPC71074
0.8478	Intermediate Similarity	NPC52021
0.8478	Intermediate Similarity	NPC25299
0.8478	Intermediate Similarity	NPC470590
0.8478	Intermediate Similarity	NPC300351
0.8478	Intermediate Similarity	NPC77099
0.8469	Intermediate Similarity	NPC284865
0.8462	Intermediate Similarity	NPC30522
0.8462	Intermediate Similarity	NPC95246
0.8462	Intermediate Similarity	NPC161751
0.8462	Intermediate Similarity	NPC474972
0.8444	Intermediate Similarity	NPC477926
0.8444	Intermediate Similarity	NPC469317
0.8444	Intermediate Similarity	NPC469314
0.8444	Intermediate Similarity	NPC241875
0.8427	Intermediate Similarity	NPC133954
0.8421	Intermediate Similarity	NPC224356
0.8421	Intermediate Similarity	NPC312075
0.8421	Intermediate Similarity	NPC189880
0.8421	Intermediate Similarity	NPC89225
0.8421	Intermediate Similarity	NPC175351
0.8421	Intermediate Similarity	NPC121402
0.8421	Intermediate Similarity	NPC21728
0.8421	Intermediate Similarity	NPC151681
0.8421	Intermediate Similarity	NPC132753
0.8421	Intermediate Similarity	NPC203343
0.8404	Intermediate Similarity	NPC180557
0.8404	Intermediate Similarity	NPC53565
0.8404	Intermediate Similarity	NPC473415

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 NPC235704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	2009
0.2-0.3	3821
0.3-0.4	2074
0.4-0.5	586
0.5-0.6	202
0.6-0.7	179
0.7-0.8	56
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8681	High Similarity	NPD7515	Phase 2
0.8421	Intermediate Similarity	NPD7902	Approved
0.8298	Intermediate Similarity	NPD7748	Approved
0.8105	Intermediate Similarity	NPD7900	Approved
0.8105	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7961	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3618	Phase 1
0.7717	Intermediate Similarity	NPD4786	Approved
0.7708	Intermediate Similarity	NPD8034	Phase 2
0.7708	Intermediate Similarity	NPD8035	Phase 2
0.7692	Intermediate Similarity	NPD3667	Approved
0.767	Intermediate Similarity	NPD7128	Approved
0.767	Intermediate Similarity	NPD5739	Approved
0.767	Intermediate Similarity	NPD6402	Approved
0.767	Intermediate Similarity	NPD6675	Approved
0.7619	Intermediate Similarity	NPD6372	Approved
0.7619	Intermediate Similarity	NPD6373	Approved
0.7556	Intermediate Similarity	NPD7645	Phase 2
0.7528	Intermediate Similarity	NPD6116	Phase 1
0.7524	Intermediate Similarity	NPD6899	Approved
0.7524	Intermediate Similarity	NPD6881	Approved
0.7524	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7455	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD4202	Approved
0.7429	Intermediate Similarity	NPD5697	Approved
0.7429	Intermediate Similarity	NPD5701	Approved
0.7416	Intermediate Similarity	NPD6117	Approved
0.7383	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD6883	Approved
0.7383	Intermediate Similarity	NPD7102	Approved
0.7353	Intermediate Similarity	NPD5286	Approved
0.7353	Intermediate Similarity	NPD5285	Approved
0.7353	Intermediate Similarity	NPD4700	Approved
0.7353	Intermediate Similarity	NPD4696	Approved
0.7347	Intermediate Similarity	NPD6079	Approved
0.7347	Intermediate Similarity	NPD6411	Approved
0.7327	Intermediate Similarity	NPD6084	Phase 2
0.7327	Intermediate Similarity	NPD6083	Phase 2
0.7315	Intermediate Similarity	NPD6869	Approved
0.7315	Intermediate Similarity	NPD8130	Phase 1
0.7315	Intermediate Similarity	NPD6847	Approved
0.7315	Intermediate Similarity	NPD6617	Approved
0.7297	Intermediate Similarity	NPD7115	Discovery
0.729	Intermediate Similarity	NPD6014	Approved
0.729	Intermediate Similarity	NPD6012	Approved
0.729	Intermediate Similarity	NPD6013	Approved
0.7283	Intermediate Similarity	NPD7525	Registered
0.7253	Intermediate Similarity	NPD6115	Approved
0.7253	Intermediate Similarity	NPD6118	Approved
0.7253	Intermediate Similarity	NPD6114	Approved
0.7253	Intermediate Similarity	NPD6697	Approved
0.7248	Intermediate Similarity	NPD8297	Approved
0.7248	Intermediate Similarity	NPD6882	Approved
0.7228	Intermediate Similarity	NPD7614	Phase 1
0.7228	Intermediate Similarity	NPD4697	Phase 3
0.7216	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5224	Approved
0.7212	Intermediate Similarity	NPD5211	Phase 2
0.7212	Intermediate Similarity	NPD4633	Approved
0.7212	Intermediate Similarity	NPD5226	Approved
0.7212	Intermediate Similarity	NPD5225	Approved
0.7196	Intermediate Similarity	NPD6011	Approved
0.7191	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5284	Approved
0.7172	Intermediate Similarity	NPD5281	Approved
0.7158	Intermediate Similarity	NPD3666	Approved
0.7158	Intermediate Similarity	NPD3133	Approved
0.7158	Intermediate Similarity	NPD3668	Phase 3
0.7158	Intermediate Similarity	NPD3665	Phase 1
0.7156	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5174	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5695	Phase 3
0.7115	Intermediate Similarity	NPD5223	Approved
0.7113	Intermediate Similarity	NPD3573	Approved
0.7087	Intermediate Similarity	NPD7638	Approved
0.7087	Intermediate Similarity	NPD5696	Approved
0.7075	Intermediate Similarity	NPD5141	Approved
0.7069	Intermediate Similarity	NPD8328	Phase 3
0.7064	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5222	Approved
0.7059	Intermediate Similarity	NPD5221	Approved
0.7019	Intermediate Similarity	NPD7639	Approved
0.7019	Intermediate Similarity	NPD7640	Approved
0.701	Intermediate Similarity	NPD7146	Approved
0.701	Intermediate Similarity	NPD7521	Approved
0.701	Intermediate Similarity	NPD7334	Approved
0.701	Intermediate Similarity	NPD5330	Approved
0.701	Intermediate Similarity	NPD6684	Approved
0.701	Intermediate Similarity	NPD6409	Approved
0.7009	Intermediate Similarity	NPD4768	Approved
0.7009	Intermediate Similarity	NPD4767	Approved
0.7009	Intermediate Similarity	NPD6008	Approved
0.699	Remote Similarity	NPD5173	Approved
0.6981	Remote Similarity	NPD4754	Approved
0.6966	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5210	Approved
0.6961	Remote Similarity	NPD4629	Approved
0.6961	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4695	Discontinued
0.6903	Remote Similarity	NPD6274	Approved
0.6893	Remote Similarity	NPD7732	Phase 3
0.6887	Remote Similarity	NPD7632	Discontinued
0.6882	Remote Similarity	NPD3617	Approved
0.6881	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4729	Approved
0.6881	Remote Similarity	NPD5128	Approved
0.6881	Remote Similarity	NPD4730	Approved
0.6875	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD4788	Approved
0.687	Remote Similarity	NPD7101	Approved
0.687	Remote Similarity	NPD7100	Approved
0.6869	Remote Similarity	NPD5737	Approved
0.6869	Remote Similarity	NPD6903	Approved
0.6869	Remote Similarity	NPD6672	Approved
0.6842	Remote Similarity	NPD4692	Approved
0.6842	Remote Similarity	NPD4139	Approved
0.6837	Remote Similarity	NPD5279	Phase 3
0.6789	Remote Similarity	NPD6412	Phase 2
0.6789	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6335	Approved
0.6771	Remote Similarity	NPD4223	Phase 3
0.6771	Remote Similarity	NPD4221	Approved
0.6765	Remote Similarity	NPD5779	Approved
0.6765	Remote Similarity	NPD5778	Approved
0.6762	Remote Similarity	NPD4225	Approved
0.6757	Remote Similarity	NPD5249	Phase 3
0.6757	Remote Similarity	NPD4634	Approved
0.6757	Remote Similarity	NPD5250	Approved
0.6757	Remote Similarity	NPD5251	Approved
0.6757	Remote Similarity	NPD5247	Approved
0.6757	Remote Similarity	NPD5248	Approved
0.6752	Remote Similarity	NPD6909	Approved
0.6752	Remote Similarity	NPD6908	Approved
0.6739	Remote Similarity	NPD6942	Approved
0.6739	Remote Similarity	NPD3703	Phase 2
0.6739	Remote Similarity	NPD7339	Approved
0.6737	Remote Similarity	NPD4748	Discontinued
0.6735	Remote Similarity	NPD5329	Approved
0.6726	Remote Similarity	NPD8133	Approved
0.6696	Remote Similarity	NPD5217	Approved
0.6696	Remote Similarity	NPD5215	Approved
0.6696	Remote Similarity	NPD6317	Approved
0.6696	Remote Similarity	NPD5216	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD4245	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6638	Remote Similarity	NPD6314	Approved
0.6638	Remote Similarity	NPD6313	Approved
0.6634	Remote Similarity	NPD6080	Approved
0.6634	Remote Similarity	NPD6904	Approved
0.6634	Remote Similarity	NPD6673	Approved
0.6633	Remote Similarity	NPD4197	Approved
0.6629	Remote Similarity	NPD5360	Phase 3
0.6629	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6868	Approved
0.6607	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5169	Approved
0.6607	Remote Similarity	NPD5135	Approved
0.6593	Remote Similarity	NPD6081	Approved
0.6591	Remote Similarity	NPD4224	Phase 2
0.6583	Remote Similarity	NPD7492	Approved
0.6566	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3698	Phase 2
0.6549	Remote Similarity	NPD5127	Approved
0.6538	Remote Similarity	NPD6001	Approved
0.6529	Remote Similarity	NPD6616	Approved
0.6529	Remote Similarity	NPD7507	Approved
0.6525	Remote Similarity	NPD6059	Approved
0.6525	Remote Similarity	NPD6054	Approved
0.6505	Remote Similarity	NPD6050	Approved
0.65	Remote Similarity	NPD4689	Approved
0.65	Remote Similarity	NPD4519	Discontinued
0.65	Remote Similarity	NPD5280	Approved
0.65	Remote Similarity	NPD4694	Approved
0.65	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD4693	Phase 3
0.65	Remote Similarity	NPD5205	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