NPASS Compound

Structure

NPC470375 OpenBabel07101719132D 34 37 0 0 1 0 0 0 0 0999 V2000 1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 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 -0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -3.0032 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 -1.7321 2.0000 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 -4.3301 0.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9074 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 21 2 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 17 30 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 27 1 0 0 0 0 23 28 1 6 0 0 0 24 27 1 0 0 0 0 24 32 1 1 0 0 0 25 29 1 1 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	6.317
LogD:	4.689
LogS:	-4.161
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	4.913
Fsp3:	0.833
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:	-5.309
MDCK Permeability:	1.292879278480541e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.829
30% Bioavailability (F30%):	0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.48
Plasma Protein Binding (PPB):	97.28199005126953%
Volume Distribution (VD):	0.695
Pgp-substrate:	2.849496841430664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.256
CYP3A4-substrate:	0.161

ADMET: Excretion

Clearance (CL):	5.561
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.427
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.144
Carcinogencity:	0.051
Eye Corrosion:	0.008
Eye Irritation:	0.069
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC470375

Natural Product ID:	NPC470375
*Common Name:**	Toosendanic Acid B
IUPAC Name:	2-[(3R,5R,9R,10R,13S,14S,16S,17S)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms:
Standard InCHIKey:	IOPZFWUTZDYRHQ-QESNHDJJSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-18(2)9-8-10-19(26(33)34)25-22(31)17-30(7)21-11-12-23-27(3,4)24(32)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,19-20,22-25,31-32H,8,10,12-17H2,1-7H3,(H,33,34)/t19?,20-,22-,23-,24+,25+,28+,29-,30+/m0/s1
SMILES:	CC(=CCCC([C@@H]1[C@@H](O)C[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@H](C2(C)C)O)C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2021462
PubChem CID:	70696018
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
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341288]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	fruits	Wanyuan County, Sichuan Province, China	2007-OCT	PMID[20961091]
NPO31089	Melia toosendan	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10000.0	nM	PMID[570191]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	<	10000.0	nM	PMID[570191]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[570191]

☑ 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 NPC470375 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	173
0.1-0.2	1137
0.2-0.3	4896
0.3-0.4	14398
0.4-0.5	7562
0.5-0.6	5582
0.6-0.7	5356
0.7-0.8	2980
0.8-0.85	470
0.85-0.9	121
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470376
0.9655	High Similarity	NPC23434
0.9551	High Similarity	NPC45324
0.9551	High Similarity	NPC162001
0.9551	High Similarity	NPC222845
0.9432	High Similarity	NPC154101
0.9425	High Similarity	NPC474704
0.9425	High Similarity	NPC475921
0.9419	High Similarity	NPC474684
0.9419	High Similarity	NPC142361
0.9333	High Similarity	NPC69548
0.9333	High Similarity	NPC184848
0.9239	High Similarity	NPC186810
0.9239	High Similarity	NPC477813
0.9239	High Similarity	NPC48647
0.9213	High Similarity	NPC86266
0.9213	High Similarity	NPC110657
0.9213	High Similarity	NPC212301
0.9213	High Similarity	NPC189520
0.9205	High Similarity	NPC54689
0.9195	High Similarity	NPC159046
0.9195	High Similarity	NPC187376
0.9195	High Similarity	NPC233836
0.9195	High Similarity	NPC312215
0.9121	High Similarity	NPC469599
0.9111	High Similarity	NPC470224
0.9111	High Similarity	NPC152897
0.9111	High Similarity	NPC141497
0.9111	High Similarity	NPC107674
0.9111	High Similarity	NPC170220
0.9111	High Similarity	NPC66429
0.9101	High Similarity	NPC471896
0.9091	High Similarity	NPC242864
0.9091	High Similarity	NPC294480
0.908	High Similarity	NPC212843
0.908	High Similarity	NPC55309
0.908	High Similarity	NPC155011
0.908	High Similarity	NPC28252
0.9022	High Similarity	NPC173272
0.9011	High Similarity	NPC49670
0.9011	High Similarity	NPC111015
0.9	High Similarity	NPC297265
0.8989	High Similarity	NPC102414
0.8989	High Similarity	NPC77168
0.8989	High Similarity	NPC84271
0.8966	High Similarity	NPC474218
0.8958	High Similarity	NPC472228
0.8958	High Similarity	NPC472227
0.8925	High Similarity	NPC107243
0.8925	High Similarity	NPC57416
0.8913	High Similarity	NPC263347
0.8913	High Similarity	NPC48330
0.8901	High Similarity	NPC243866
0.8889	High Similarity	NPC227467
0.8889	High Similarity	NPC273621
0.8889	High Similarity	NPC477872
0.8889	High Similarity	NPC7260
0.8889	High Similarity	NPC18872
0.8889	High Similarity	NPC175628
0.8889	High Similarity	NPC290614
0.8889	High Similarity	NPC111585
0.8889	High Similarity	NPC46281
0.8889	High Similarity	NPC469400
0.8889	High Similarity	NPC120968
0.8889	High Similarity	NPC210037
0.8889	High Similarity	NPC148414
0.8876	High Similarity	NPC183546
0.8876	High Similarity	NPC48866
0.8876	High Similarity	NPC247406
0.8864	High Similarity	NPC73038
0.8854	High Similarity	NPC140723
0.8851	High Similarity	NPC82902
0.883	High Similarity	NPC477854
0.8817	High Similarity	NPC477853
0.8817	High Similarity	NPC155676
0.8804	High Similarity	NPC469406
0.8804	High Similarity	NPC159410
0.8791	High Similarity	NPC187722
0.8791	High Similarity	NPC26888
0.8791	High Similarity	NPC105189
0.8778	High Similarity	NPC290972
0.8778	High Similarity	NPC25906
0.8778	High Similarity	NPC215029
0.8778	High Similarity	NPC64872
0.8778	High Similarity	NPC476733
0.8778	High Similarity	NPC128496
0.8778	High Similarity	NPC477943
0.8778	High Similarity	NPC474889
0.8778	High Similarity	NPC155479
0.8764	High Similarity	NPC96496
0.8764	High Similarity	NPC317590
0.8764	High Similarity	NPC477926
0.8763	High Similarity	NPC477812
0.875	High Similarity	NPC22388
0.8737	High Similarity	NPC154072
0.8737	High Similarity	NPC218383
0.8723	High Similarity	NPC475894
0.8723	High Similarity	NPC108078
0.8723	High Similarity	NPC190554
0.871	High Similarity	NPC279974
0.871	High Similarity	NPC472485
0.8696	High Similarity	NPC202728
0.8696	High Similarity	NPC118519
0.8696	High Similarity	NPC229281
0.8696	High Similarity	NPC477855
0.8696	High Similarity	NPC158059
0.8696	High Similarity	NPC475255
0.8681	High Similarity	NPC44240
0.8681	High Similarity	NPC291028
0.8681	High Similarity	NPC193750
0.8681	High Similarity	NPC130278
0.8681	High Similarity	NPC171441
0.8681	High Similarity	NPC123854
0.8673	High Similarity	NPC278628
0.8673	High Similarity	NPC231530
0.8667	High Similarity	NPC474719
0.8667	High Similarity	NPC182797
0.8667	High Similarity	NPC328313
0.8667	High Similarity	NPC52169
0.8652	High Similarity	NPC474970
0.8652	High Similarity	NPC2783
0.8652	High Similarity	NPC469994
0.8652	High Similarity	NPC94755
0.8652	High Similarity	NPC325594
0.8646	High Similarity	NPC474327
0.8636	High Similarity	NPC165064
0.8636	High Similarity	NPC59453
0.8636	High Similarity	NPC221758
0.8632	High Similarity	NPC194196
0.8617	High Similarity	NPC95565
0.8617	High Similarity	NPC235053
0.8602	High Similarity	NPC166906
0.8602	High Similarity	NPC6818
0.8602	High Similarity	NPC191412
0.8602	High Similarity	NPC114159
0.8587	High Similarity	NPC38754
0.8587	High Similarity	NPC45269
0.8586	High Similarity	NPC64844
0.8586	High Similarity	NPC42847
0.8571	High Similarity	NPC121798
0.8571	High Similarity	NPC263393
0.8571	High Similarity	NPC76879
0.8571	High Similarity	NPC474245
0.8571	High Similarity	NPC274330
0.8571	High Similarity	NPC130520
0.8571	High Similarity	NPC293048
0.8571	High Similarity	NPC474679
0.8571	High Similarity	NPC127689
0.8571	High Similarity	NPC198664
0.8571	High Similarity	NPC234346
0.8571	High Similarity	NPC1015
0.8571	High Similarity	NPC61543
0.8571	High Similarity	NPC225585
0.8571	High Similarity	NPC270768
0.8571	High Similarity	NPC32830
0.8571	High Similarity	NPC31985
0.8571	High Similarity	NPC59263
0.8571	High Similarity	NPC143232
0.8571	High Similarity	NPC29705
0.8557	High Similarity	NPC193934
0.8557	High Similarity	NPC271980
0.8557	High Similarity	NPC195290
0.8557	High Similarity	NPC136289
0.8557	High Similarity	NPC204450
0.8556	High Similarity	NPC242468
0.8556	High Similarity	NPC171203
0.8556	High Similarity	NPC307426
0.8556	High Similarity	NPC269360
0.8556	High Similarity	NPC88716
0.8556	High Similarity	NPC264005
0.8556	High Similarity	NPC102683
0.8556	High Similarity	NPC68160
0.8556	High Similarity	NPC142415
0.8556	High Similarity	NPC167877
0.8556	High Similarity	NPC18064
0.8556	High Similarity	NPC33768
0.8556	High Similarity	NPC98442
0.8556	High Similarity	NPC51700
0.8556	High Similarity	NPC475740
0.8556	High Similarity	NPC293564
0.8556	High Similarity	NPC130577
0.8542	High Similarity	NPC15390
0.8539	High Similarity	NPC470574
0.8539	High Similarity	NPC264317
0.8539	High Similarity	NPC294438
0.8526	High Similarity	NPC18509
0.8523	High Similarity	NPC245866
0.8511	High Similarity	NPC317586
0.8511	High Similarity	NPC205173
0.8511	High Similarity	NPC53565
0.8511	High Similarity	NPC96916
0.8511	High Similarity	NPC470016
0.8506	High Similarity	NPC147066
0.8506	High Similarity	NPC473420
0.85	High Similarity	NPC94529
0.8495	Intermediate Similarity	NPC206810
0.8495	Intermediate Similarity	NPC474436
0.8495	Intermediate Similarity	NPC63118
0.8495	Intermediate Similarity	NPC118490
0.8495	Intermediate Similarity	NPC49776

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 NPC470375 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1457
0.2-0.3	3982
0.3-0.4	2423
0.4-0.5	618
0.5-0.6	180
0.6-0.7	137
0.7-0.8	126
0.8-0.85	59
0.85-0.9	21
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8901	High Similarity	NPD6399	Phase 3
0.8696	High Similarity	NPD4202	Approved
0.8673	High Similarity	NPD7128	Approved
0.8673	High Similarity	NPD6675	Approved
0.8673	High Similarity	NPD6402	Approved
0.8673	High Similarity	NPD5739	Approved
0.8652	High Similarity	NPD3618	Phase 1
0.8636	High Similarity	NPD4786	Approved
0.86	High Similarity	NPD6373	Approved
0.86	High Similarity	NPD6372	Approved
0.8571	High Similarity	NPD5328	Approved
0.8539	High Similarity	NPD7520	Clinical (unspecified phase)
0.8526	High Similarity	NPD4755	Approved
0.85	High Similarity	NPD7320	Approved
0.85	High Similarity	NPD6899	Approved
0.85	High Similarity	NPD6881	Approved
0.8431	Intermediate Similarity	NPD6649	Approved
0.8431	Intermediate Similarity	NPD6650	Approved
0.8427	Intermediate Similarity	NPD3665	Phase 1
0.8427	Intermediate Similarity	NPD3133	Approved
0.8427	Intermediate Similarity	NPD3666	Approved
0.8409	Intermediate Similarity	NPD3667	Approved
0.84	Intermediate Similarity	NPD5697	Approved
0.84	Intermediate Similarity	NPD5701	Approved
0.8387	Intermediate Similarity	NPD7515	Phase 2
0.8387	Intermediate Similarity	NPD6079	Approved
0.8387	Intermediate Similarity	NPD8035	Phase 2
0.8387	Intermediate Similarity	NPD8034	Phase 2
0.8351	Intermediate Similarity	NPD4700	Approved
0.8351	Intermediate Similarity	NPD4696	Approved
0.8351	Intermediate Similarity	NPD5285	Approved
0.8351	Intermediate Similarity	NPD5286	Approved
0.8333	Intermediate Similarity	NPD6084	Phase 2
0.8333	Intermediate Similarity	NPD7290	Approved
0.8333	Intermediate Similarity	NPD6083	Phase 2
0.8333	Intermediate Similarity	NPD6883	Approved
0.8333	Intermediate Similarity	NPD7102	Approved
0.8317	Intermediate Similarity	NPD6011	Approved
0.8265	Intermediate Similarity	NPD5223	Approved
0.8252	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD6617	Approved
0.8252	Intermediate Similarity	NPD8130	Phase 1
0.8252	Intermediate Similarity	NPD6847	Approved
0.8252	Intermediate Similarity	NPD6869	Approved
0.8242	Intermediate Similarity	NPD6684	Approved
0.8242	Intermediate Similarity	NPD7334	Approved
0.8242	Intermediate Similarity	NPD7521	Approved
0.8242	Intermediate Similarity	NPD5330	Approved
0.8242	Intermediate Similarity	NPD6409	Approved
0.8242	Intermediate Similarity	NPD7146	Approved
0.8235	Intermediate Similarity	NPD6013	Approved
0.8235	Intermediate Similarity	NPD6012	Approved
0.8235	Intermediate Similarity	NPD6014	Approved
0.8229	Intermediate Similarity	NPD4697	Phase 3
0.8191	Intermediate Similarity	NPD5281	Approved
0.8191	Intermediate Similarity	NPD5284	Approved
0.8182	Intermediate Similarity	NPD5226	Approved
0.8182	Intermediate Similarity	NPD5211	Phase 2
0.8182	Intermediate Similarity	NPD7525	Registered
0.8182	Intermediate Similarity	NPD5225	Approved
0.8182	Intermediate Similarity	NPD4633	Approved
0.8182	Intermediate Similarity	NPD5224	Approved
0.8173	Intermediate Similarity	NPD6882	Approved
0.8173	Intermediate Similarity	NPD8297	Approved
0.8172	Intermediate Similarity	NPD4753	Phase 2
0.8144	Intermediate Similarity	NPD7902	Approved
0.8125	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD5175	Approved
0.81	Intermediate Similarity	NPD5174	Approved
0.81	Intermediate Similarity	NPD4754	Approved
0.8065	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD6903	Approved
0.8061	Intermediate Similarity	NPD7638	Approved
0.8061	Intermediate Similarity	NPD5696	Approved
0.8046	Intermediate Similarity	NPD6116	Phase 1
0.8041	Intermediate Similarity	NPD5221	Approved
0.8041	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5222	Approved
0.8021	Intermediate Similarity	NPD7748	Approved
0.802	Intermediate Similarity	NPD5141	Approved
0.8	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4223	Phase 3
0.798	Intermediate Similarity	NPD7639	Approved
0.798	Intermediate Similarity	NPD7640	Approved
0.7959	Intermediate Similarity	NPD5173	Approved
0.7941	Intermediate Similarity	NPD6008	Approved
0.7941	Intermediate Similarity	NPD4768	Approved
0.7941	Intermediate Similarity	NPD4767	Approved
0.7938	Intermediate Similarity	NPD5210	Approved
0.7938	Intermediate Similarity	NPD4629	Approved
0.7938	Intermediate Similarity	NPD5695	Phase 3
0.7935	Intermediate Similarity	NPD5329	Approved
0.7931	Intermediate Similarity	NPD6117	Approved
0.7931	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4632	Approved
0.7872	Intermediate Similarity	NPD6672	Approved
0.7872	Intermediate Similarity	NPD5737	Approved
0.7849	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6098	Approved
0.7835	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD7900	Approved
0.7826	Intermediate Similarity	NPD4197	Approved
0.7826	Intermediate Similarity	NPD3668	Phase 3
0.7816	Intermediate Similarity	NPD6942	Approved
0.7816	Intermediate Similarity	NPD7339	Approved
0.7798	Intermediate Similarity	NPD6335	Approved
0.7789	Intermediate Similarity	NPD6904	Approved
0.7789	Intermediate Similarity	NPD6080	Approved
0.7789	Intermediate Similarity	NPD6673	Approved
0.7788	Intermediate Similarity	NPD4730	Approved
0.7788	Intermediate Similarity	NPD4729	Approved
0.7788	Intermediate Similarity	NPD5128	Approved
0.7778	Intermediate Similarity	NPD6274	Approved
0.7753	Intermediate Similarity	NPD6697	Approved
0.7753	Intermediate Similarity	NPD6115	Approved
0.7753	Intermediate Similarity	NPD6114	Approved
0.7753	Intermediate Similarity	NPD6118	Approved
0.7727	Intermediate Similarity	NPD7100	Approved
0.7727	Intermediate Similarity	NPD7101	Approved
0.7717	Intermediate Similarity	NPD4788	Approved
0.7706	Intermediate Similarity	NPD6009	Approved
0.7706	Intermediate Similarity	NPD6317	Approved
0.7701	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4689	Approved
0.766	Intermediate Similarity	NPD4693	Phase 3
0.766	Intermediate Similarity	NPD4690	Approved
0.766	Intermediate Similarity	NPD5205	Approved
0.766	Intermediate Similarity	NPD4688	Approved
0.766	Intermediate Similarity	NPD4138	Approved
0.766	Intermediate Similarity	NPD5279	Phase 3
0.7653	Intermediate Similarity	NPD6001	Approved
0.7642	Intermediate Similarity	NPD5250	Approved
0.7642	Intermediate Similarity	NPD5249	Phase 3
0.7642	Intermediate Similarity	NPD5248	Approved
0.7642	Intermediate Similarity	NPD5247	Approved
0.7642	Intermediate Similarity	NPD5169	Approved
0.7642	Intermediate Similarity	NPD5251	Approved
0.7642	Intermediate Similarity	NPD4634	Approved
0.7642	Intermediate Similarity	NPD5135	Approved
0.7642	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6313	Approved
0.7636	Intermediate Similarity	NPD6314	Approved
0.7589	Intermediate Similarity	NPD6908	Approved
0.7589	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6909	Approved
0.757	Intermediate Similarity	NPD5217	Approved
0.757	Intermediate Similarity	NPD5216	Approved
0.757	Intermediate Similarity	NPD5127	Approved
0.757	Intermediate Similarity	NPD5215	Approved
0.7545	Intermediate Similarity	NPD7115	Discovery
0.7524	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD5208	Approved
0.75	Intermediate Similarity	NPD6319	Approved
0.7474	Intermediate Similarity	NPD5690	Phase 2
0.7474	Intermediate Similarity	NPD5280	Approved
0.7474	Intermediate Similarity	NPD4694	Approved
0.7471	Intermediate Similarity	NPD4243	Approved
0.7456	Intermediate Similarity	NPD7604	Phase 2
0.7455	Intermediate Similarity	NPD6868	Approved
0.7449	Intermediate Similarity	NPD6050	Approved
0.7449	Intermediate Similarity	NPD5693	Phase 1
0.7434	Intermediate Similarity	NPD5983	Phase 2
0.7423	Intermediate Similarity	NPD6051	Approved
0.7391	Intermediate Similarity	NPD7492	Approved
0.7391	Intermediate Similarity	NPD5368	Approved
0.7364	Intermediate Similarity	NPD5167	Approved
0.7363	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5207	Approved
0.7347	Intermediate Similarity	NPD5692	Phase 3
0.7345	Intermediate Similarity	NPD6054	Approved
0.7345	Intermediate Similarity	NPD6059	Approved
0.734	Intermediate Similarity	NPD5362	Discontinued
0.7328	Intermediate Similarity	NPD6616	Approved
0.7328	Intermediate Similarity	NPD6336	Discontinued
0.7312	Intermediate Similarity	NPD4139	Approved
0.7312	Intermediate Similarity	NPD4692	Approved
0.7312	Intermediate Similarity	NPD5369	Approved
0.7308	Intermediate Similarity	NPD7632	Discontinued
0.7303	Intermediate Similarity	NPD4784	Approved
0.7303	Intermediate Similarity	NPD4785	Approved
0.729	Intermediate Similarity	NPD5168	Approved
0.7283	Intermediate Similarity	NPD7645	Phase 2
0.7283	Intermediate Similarity	NPD4195	Approved
0.7273	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5694	Approved
0.7273	Intermediate Similarity	NPD6411	Approved
0.7273	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7078	Approved
0.7265	Intermediate Similarity	NPD8293	Discontinued
0.7234	Intermediate Similarity	NPD6435	Approved
0.7234	Intermediate Similarity	NPD4269	Approved
0.7234	Intermediate Similarity	NPD4270	Approved
0.7217	Intermediate Similarity	NPD6370	Approved
0.7216	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4748	Discontinued
0.7203	Intermediate Similarity	NPD7736	Approved
0.7179	Intermediate Similarity	NPD7507	Approved
0.7174	Intermediate Similarity	NPD3617	Approved
0.7159	Intermediate Similarity	NPD4245	Approved
0.7159	Intermediate Similarity	NPD4244	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