NPASS Compound

Structure

NPC196485 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5180 4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -3.8660 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1871 4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 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 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5909 2.0032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 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 0.2308 3.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3872 1.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 16 25 1 0 0 0 0 18 3 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 30 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 28 1 1 0 0 0 22 26 1 0 0 0 0 22 31 2 0 0 0 0 23 27 1 0 0 0 0 23 28 1 1 0 0 0 24 27 1 0 0 0 0 24 32 1 1 0 0 0 25 30 1 1 0 0 0 25 33 1 0 0 0 0 26 34 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	520.462
LogP:	4.877
LogD:	4.585
LogS:	-5.261
# Rotatable Bonds:	5
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.395
Synthetic Accessibility Score:	5.041
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.841
MDCK Permeability:	2.5585717594367452e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.79
30% Bioavailability (F30%):	0.379

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.21
Plasma Protein Binding (PPB):	98.81501770019531%
Volume Distribution (VD):	0.685
Pgp-substrate:	2.5125584602355957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.191
CYP2C19-substrate:	0.846
CYP2C9-inhibitor:	0.302
CYP2C9-substrate:	0.461
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.53
CYP3A4-substrate:	0.474

ADMET: Excretion

Clearance (CL):	7.737
Half-life (T1/2):	0.083

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.162
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.616
Maximum Recommended Daily Dose:	0.95
Skin Sensitization:	0.213
Carcinogencity:	0.024
Eye Corrosion:	0.006
Eye Irritation:	0.086
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC196485

Natural Product ID:	NPC196485
*Common Name:**	Mesendanin S
IUPAC Name:	(5S,6R)-6-[(3S,5R,9R,10R,12R,13S,14R,17S)-3,12-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-2-methylhept-2-en-4-one
Synonyms:
Standard InCHIKey:	RWTYEJPLFNVDNC-HLEYRIMWSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-17(2)15-22(31)26(34)18(3)19-11-14-29(7)20-9-10-23-27(4,5)24(32)12-13-28(23,6)21(20)16-25(33)30(19,29)8/h9,15,18-19,21,23-26,32-34H,10-14,16H2,1-8H3/t18-,19+,21+,23+,24+,25-,26+,28-,29-,30-/m1/s1
SMILES:	CC(=CC(=O)[C@H]([C@@H]([C@@H]1CC[C@]2([C@@]1(C)[C@H](O)C[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409066
PubChem CID:	73352160
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
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23795939]
NPO8774	Walsura cochinchinensis	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	2
Others	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4862	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	IC50	=	1150.0	nM	PMID[569873]
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	IC50	=	3740.0	nM	PMID[569873]
NPT4862	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Mus musculus	Inhibition	>	60.0	%	PMID[569873]
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	>	60.0	%	PMID[569873]

☑ 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 NPC196485 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	172
0.1-0.2	1165
0.2-0.3	4585
0.3-0.4	11544
0.4-0.5	10490
0.5-0.6	6112
0.6-0.7	5231
0.7-0.8	2959
0.8-0.85	308
0.85-0.9	102
0.9-0.95	27
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC245972
0.9333	High Similarity	NPC111015
0.9326	High Similarity	NPC168027
0.9326	High Similarity	NPC185936
0.9318	High Similarity	NPC186688
0.9318	High Similarity	NPC31985
0.9318	High Similarity	NPC1015
0.9318	High Similarity	NPC474245
0.931	High Similarity	NPC475740
0.9239	High Similarity	NPC108078
0.9222	High Similarity	NPC12722
0.9205	High Similarity	NPC471722
0.9195	High Similarity	NPC474733
0.9195	High Similarity	NPC474732
0.9195	High Similarity	NPC145879
0.9195	High Similarity	NPC51014
0.9195	High Similarity	NPC31564
0.9195	High Similarity	NPC474778
0.9158	High Similarity	NPC247957
0.9158	High Similarity	NPC249187
0.9091	High Similarity	NPC58063
0.908	High Similarity	NPC470574
0.9062	High Similarity	NPC72255
0.9043	High Similarity	NPC15390
0.9043	High Similarity	NPC327431
0.9022	High Similarity	NPC271195
0.9011	High Similarity	NPC475255
0.9	High Similarity	NPC48010
0.8989	High Similarity	NPC328539
0.8989	High Similarity	NPC193360
0.8977	High Similarity	NPC72133
0.8969	High Similarity	NPC257353
0.8966	High Similarity	NPC59453
0.8966	High Similarity	NPC214043
0.8966	High Similarity	NPC85774
0.8966	High Similarity	NPC221758
0.8966	High Similarity	NPC237712
0.8936	High Similarity	NPC114274
0.8925	High Similarity	NPC305483
0.8925	High Similarity	NPC96859
0.8925	High Similarity	NPC328162
0.8925	High Similarity	NPC192428
0.8901	High Similarity	NPC233116
0.8901	High Similarity	NPC272746
0.8901	High Similarity	NPC473998
0.8901	High Similarity	NPC131872
0.8889	High Similarity	NPC86319
0.8889	High Similarity	NPC32830
0.8889	High Similarity	NPC473999
0.8889	High Similarity	NPC119416
0.8889	High Similarity	NPC275740
0.8889	High Similarity	NPC268406
0.8889	High Similarity	NPC26959
0.8889	High Similarity	NPC309603
0.8889	High Similarity	NPC76879
0.8864	High Similarity	NPC469948
0.8864	High Similarity	NPC197823
0.8842	High Similarity	NPC154072
0.883	High Similarity	NPC320306
0.883	High Similarity	NPC18509
0.883	High Similarity	NPC190554
0.8791	High Similarity	NPC191684
0.8791	High Similarity	NPC85173
0.8791	High Similarity	NPC126993
0.8778	High Similarity	NPC131470
0.8778	High Similarity	NPC143767
0.8764	High Similarity	NPC20688
0.8764	High Similarity	NPC222613
0.8764	High Similarity	NPC327115
0.8764	High Similarity	NPC118648
0.8764	High Similarity	NPC475022
0.8763	High Similarity	NPC191892
0.875	High Similarity	NPC472265
0.875	High Similarity	NPC473246
0.8737	High Similarity	NPC191565
0.8737	High Similarity	NPC103051
0.8736	High Similarity	NPC151519
0.8736	High Similarity	NPC48362
0.8723	High Similarity	NPC49371
0.871	High Similarity	NPC23170
0.871	High Similarity	NPC8993
0.871	High Similarity	NPC166906
0.8696	High Similarity	NPC155304
0.8696	High Similarity	NPC475806
0.8687	High Similarity	NPC472925
0.8681	High Similarity	NPC477943
0.8681	High Similarity	NPC475921
0.8681	High Similarity	NPC310010
0.8681	High Similarity	NPC326627
0.8681	High Similarity	NPC474704
0.8667	High Similarity	NPC142361
0.8667	High Similarity	NPC141292
0.8667	High Similarity	NPC474684
0.8646	High Similarity	NPC144956
0.8632	High Similarity	NPC43747
0.8617	High Similarity	NPC472485
0.8617	High Similarity	NPC473170
0.8617	High Similarity	NPC317586
0.8617	High Similarity	NPC200702
0.8617	High Similarity	NPC127063
0.8617	High Similarity	NPC470016
0.8617	High Similarity	NPC280725
0.8602	High Similarity	NPC69454
0.8587	High Similarity	NPC46758
0.8587	High Similarity	NPC183283
0.8586	High Similarity	NPC149047
0.8586	High Similarity	NPC166607
0.8571	High Similarity	NPC292491
0.8571	High Similarity	NPC53911
0.8571	High Similarity	NPC310752
0.8571	High Similarity	NPC471724
0.8571	High Similarity	NPC242864
0.8571	High Similarity	NPC328313
0.8571	High Similarity	NPC474677
0.8571	High Similarity	NPC230387
0.8556	High Similarity	NPC94666
0.8556	High Similarity	NPC472985
0.8556	High Similarity	NPC155011
0.8556	High Similarity	NPC472986
0.8556	High Similarity	NPC94755
0.8539	High Similarity	NPC33913
0.8539	High Similarity	NPC321187
0.8539	High Similarity	NPC329043
0.8539	High Similarity	NPC82902
0.8539	High Similarity	NPC161423
0.8539	High Similarity	NPC227064
0.8539	High Similarity	NPC58841
0.8526	High Similarity	NPC249954
0.8526	High Similarity	NPC173272
0.8511	High Similarity	NPC209662
0.8511	High Similarity	NPC474690
0.8511	High Similarity	NPC474328
0.8511	High Similarity	NPC471207
0.8506	High Similarity	NPC2482
0.85	High Similarity	NPC220229
0.85	High Similarity	NPC165873
0.85	High Similarity	NPC475060
0.8495	Intermediate Similarity	NPC212301
0.8495	Intermediate Similarity	NPC63748
0.8495	Intermediate Similarity	NPC86266
0.8495	Intermediate Similarity	NPC110657
0.8495	Intermediate Similarity	NPC189520
0.8485	Intermediate Similarity	NPC209502
0.8485	Intermediate Similarity	NPC160843
0.8485	Intermediate Similarity	NPC204833
0.8478	Intermediate Similarity	NPC122116
0.8478	Intermediate Similarity	NPC250592
0.8478	Intermediate Similarity	NPC77263
0.8469	Intermediate Similarity	NPC22388
0.8469	Intermediate Similarity	NPC477054
0.8469	Intermediate Similarity	NPC234892
0.8469	Intermediate Similarity	NPC293753
0.8462	Intermediate Similarity	NPC233836
0.8462	Intermediate Similarity	NPC187376
0.8462	Intermediate Similarity	NPC90652
0.8462	Intermediate Similarity	NPC159046
0.8462	Intermediate Similarity	NPC93778
0.8462	Intermediate Similarity	NPC317590
0.8454	Intermediate Similarity	NPC83709
0.8454	Intermediate Similarity	NPC474720
0.8447	Intermediate Similarity	NPC71348
0.8444	Intermediate Similarity	NPC474218
0.8444	Intermediate Similarity	NPC471224
0.8431	Intermediate Similarity	NPC163314
0.8427	Intermediate Similarity	NPC278648
0.8427	Intermediate Similarity	NPC476082
0.8421	Intermediate Similarity	NPC297199
0.8421	Intermediate Similarity	NPC279974
0.8421	Intermediate Similarity	NPC48330
0.8421	Intermediate Similarity	NPC259286
0.8416	Intermediate Similarity	NPC94529
0.8416	Intermediate Similarity	NPC217201
0.8404	Intermediate Similarity	NPC211230
0.8404	Intermediate Similarity	NPC472930
0.8404	Intermediate Similarity	NPC170220
0.8404	Intermediate Similarity	NPC134826
0.8404	Intermediate Similarity	NPC470376
0.8404	Intermediate Similarity	NPC474736
0.8404	Intermediate Similarity	NPC141497
0.8404	Intermediate Similarity	NPC477855
0.8404	Intermediate Similarity	NPC107674
0.8404	Intermediate Similarity	NPC470375
0.8404	Intermediate Similarity	NPC109305
0.8404	Intermediate Similarity	NPC233118
0.84	Intermediate Similarity	NPC296945
0.84	Intermediate Similarity	NPC48733
0.84	Intermediate Similarity	NPC85829
0.84	Intermediate Similarity	NPC260268
0.84	Intermediate Similarity	NPC150531
0.84	Intermediate Similarity	NPC49958
0.84	Intermediate Similarity	NPC302607
0.84	Intermediate Similarity	NPC152695
0.84	Intermediate Similarity	NPC476027
0.84	Intermediate Similarity	NPC97202
0.84	Intermediate Similarity	NPC214264
0.84	Intermediate Similarity	NPC319077
0.84	Intermediate Similarity	NPC50692
0.84	Intermediate Similarity	NPC171137
0.84	Intermediate Similarity	NPC202167
0.8387	Intermediate Similarity	NPC129913

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 NPC196485 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1461
0.2-0.3	3970
0.3-0.4	2412
0.4-0.5	666
0.5-0.6	164
0.6-0.7	102
0.7-0.8	139
0.8-0.85	55
0.85-0.9	23
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9101	High Similarity	NPD5328	Approved
0.8977	High Similarity	NPD3618	Phase 1
0.8966	High Similarity	NPD4786	Approved
0.8925	High Similarity	NPD5221	Approved
0.8925	High Similarity	NPD5222	Approved
0.8925	High Similarity	NPD5220	Clinical (unspecified phase)
0.8925	High Similarity	NPD4697	Phase 3
0.8901	High Similarity	NPD6079	Approved
0.883	High Similarity	NPD4755	Approved
0.883	High Similarity	NPD5173	Approved
0.8736	High Similarity	NPD3667	Approved
0.8681	High Similarity	NPD4753	Phase 2
0.8646	High Similarity	NPD5286	Approved
0.8646	High Similarity	NPD5285	Approved
0.8646	High Similarity	NPD4700	Approved
0.8646	High Similarity	NPD4696	Approved
0.8602	High Similarity	NPD4202	Approved
0.8557	High Similarity	NPD5223	Approved
0.8556	High Similarity	NPD5279	Phase 3
0.8539	High Similarity	NPD3665	Phase 1
0.8539	High Similarity	NPD3133	Approved
0.8539	High Similarity	NPD3666	Approved
0.8469	Intermediate Similarity	NPD5226	Approved
0.8469	Intermediate Similarity	NPD5225	Approved
0.8469	Intermediate Similarity	NPD4633	Approved
0.8469	Intermediate Similarity	NPD5211	Phase 2
0.8469	Intermediate Similarity	NPD5224	Approved
0.8444	Intermediate Similarity	NPD5329	Approved
0.84	Intermediate Similarity	NPD5739	Approved
0.84	Intermediate Similarity	NPD6675	Approved
0.84	Intermediate Similarity	NPD7128	Approved
0.84	Intermediate Similarity	NPD6402	Approved
0.8384	Intermediate Similarity	NPD5174	Approved
0.8384	Intermediate Similarity	NPD5175	Approved
0.8384	Intermediate Similarity	NPD4754	Approved
0.8333	Intermediate Similarity	NPD4197	Approved
0.83	Intermediate Similarity	NPD5141	Approved
0.8298	Intermediate Similarity	NPD7515	Phase 2
0.8252	Intermediate Similarity	NPD4634	Approved
0.8247	Intermediate Similarity	NPD6084	Phase 2
0.8247	Intermediate Similarity	NPD6083	Phase 2
0.8235	Intermediate Similarity	NPD7320	Approved
0.8235	Intermediate Similarity	NPD6881	Approved
0.8235	Intermediate Similarity	NPD6899	Approved
0.8229	Intermediate Similarity	NPD5210	Approved
0.8229	Intermediate Similarity	NPD4629	Approved
0.8218	Intermediate Similarity	NPD4768	Approved
0.8218	Intermediate Similarity	NPD4767	Approved
0.8211	Intermediate Similarity	NPD6399	Phase 3
0.8172	Intermediate Similarity	NPD5737	Approved
0.8172	Intermediate Similarity	NPD6672	Approved
0.8155	Intermediate Similarity	NPD6373	Approved
0.8155	Intermediate Similarity	NPD6372	Approved
0.8137	Intermediate Similarity	NPD5697	Approved
0.8137	Intermediate Similarity	NPD5701	Approved
0.8132	Intermediate Similarity	NPD3668	Phase 3
0.8111	Intermediate Similarity	NPD4221	Approved
0.8111	Intermediate Similarity	NPD4223	Phase 3
0.809	Intermediate Similarity	NPD4695	Discontinued
0.8077	Intermediate Similarity	NPD7290	Approved
0.8077	Intermediate Similarity	NPD7102	Approved
0.8077	Intermediate Similarity	NPD6883	Approved
0.8068	Intermediate Similarity	NPD3617	Approved
0.8058	Intermediate Similarity	NPD5128	Approved
0.8058	Intermediate Similarity	NPD4729	Approved
0.8058	Intermediate Similarity	NPD6011	Approved
0.8058	Intermediate Similarity	NPD5168	Approved
0.8058	Intermediate Similarity	NPD4730	Approved
0.8019	Intermediate Similarity	NPD4632	Approved
0.8	Intermediate Similarity	NPD6869	Approved
0.8	Intermediate Similarity	NPD6649	Approved
0.8	Intermediate Similarity	NPD6617	Approved
0.8	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6650	Approved
0.8	Intermediate Similarity	NPD6847	Approved
0.8	Intermediate Similarity	NPD8130	Phase 1
0.7981	Intermediate Similarity	NPD6013	Approved
0.7981	Intermediate Similarity	NPD6014	Approved
0.7981	Intermediate Similarity	NPD6012	Approved
0.798	Intermediate Similarity	NPD7638	Approved
0.7957	Intermediate Similarity	NPD4694	Approved
0.7957	Intermediate Similarity	NPD5690	Phase 2
0.7957	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD5280	Approved
0.7938	Intermediate Similarity	NPD7748	Approved
0.7931	Intermediate Similarity	NPD6942	Approved
0.7931	Intermediate Similarity	NPD7339	Approved
0.7925	Intermediate Similarity	NPD6882	Approved
0.7925	Intermediate Similarity	NPD8297	Approved
0.7905	Intermediate Similarity	NPD5248	Approved
0.7905	Intermediate Similarity	NPD5250	Approved
0.7905	Intermediate Similarity	NPD5249	Phase 3
0.7905	Intermediate Similarity	NPD5169	Approved
0.7905	Intermediate Similarity	NPD5251	Approved
0.7905	Intermediate Similarity	NPD5247	Approved
0.7905	Intermediate Similarity	NPD5135	Approved
0.7905	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD7640	Approved
0.79	Intermediate Similarity	NPD7639	Approved
0.7889	Intermediate Similarity	NPD7525	Registered
0.7857	Intermediate Similarity	NPD5695	Phase 3
0.7849	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.783	Intermediate Similarity	NPD5215	Approved
0.783	Intermediate Similarity	NPD5217	Approved
0.783	Intermediate Similarity	NPD5127	Approved
0.783	Intermediate Similarity	NPD5216	Approved
0.78	Intermediate Similarity	NPD5696	Approved
0.7798	Intermediate Similarity	NPD6009	Approved
0.7766	Intermediate Similarity	NPD4689	Approved
0.7766	Intermediate Similarity	NPD5330	Approved
0.7766	Intermediate Similarity	NPD4693	Phase 3
0.7766	Intermediate Similarity	NPD4138	Approved
0.7766	Intermediate Similarity	NPD4688	Approved
0.7766	Intermediate Similarity	NPD7521	Approved
0.7766	Intermediate Similarity	NPD4690	Approved
0.7766	Intermediate Similarity	NPD7334	Approved
0.7766	Intermediate Similarity	NPD6684	Approved
0.7766	Intermediate Similarity	NPD5205	Approved
0.7766	Intermediate Similarity	NPD6409	Approved
0.7766	Intermediate Similarity	NPD7146	Approved
0.7748	Intermediate Similarity	NPD6054	Approved
0.7748	Intermediate Similarity	NPD6059	Approved
0.7708	Intermediate Similarity	NPD6673	Approved
0.7708	Intermediate Similarity	NPD6080	Approved
0.7708	Intermediate Similarity	NPD6904	Approved
0.7706	Intermediate Similarity	NPD6868	Approved
0.77	Intermediate Similarity	NPD7902	Approved
0.7692	Intermediate Similarity	NPD6008	Approved
0.764	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4788	Approved
0.7619	Intermediate Similarity	NPD6412	Phase 2
0.7615	Intermediate Similarity	NPD5167	Approved
0.7611	Intermediate Similarity	NPD6370	Approved
0.7604	Intermediate Similarity	NPD6903	Approved
0.7604	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6319	Approved
0.7568	Intermediate Similarity	NPD6335	Approved
0.7545	Intermediate Similarity	NPD6274	Approved
0.7544	Intermediate Similarity	NPD7604	Phase 2
0.7526	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6016	Approved
0.7522	Intermediate Similarity	NPD5983	Phase 2
0.7522	Intermediate Similarity	NPD6015	Approved
0.75	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD7101	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD7492	Approved
0.7477	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD6317	Approved
0.7473	Intermediate Similarity	NPD6697	Approved
0.7473	Intermediate Similarity	NPD6115	Approved
0.7473	Intermediate Similarity	NPD6118	Approved
0.7473	Intermediate Similarity	NPD6114	Approved
0.7471	Intermediate Similarity	NPD4747	Approved
0.7456	Intermediate Similarity	NPD5988	Approved
0.7414	Intermediate Similarity	NPD6616	Approved
0.7414	Intermediate Similarity	NPD6336	Discontinued
0.7411	Intermediate Similarity	NPD6313	Approved
0.7411	Intermediate Similarity	NPD6314	Approved
0.74	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7900	Approved
0.7396	Intermediate Similarity	NPD6098	Approved
0.7391	Intermediate Similarity	NPD4195	Approved
0.7386	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD5693	Phase 1
0.7374	Intermediate Similarity	NPD5281	Approved
0.7374	Intermediate Similarity	NPD5284	Approved
0.7374	Intermediate Similarity	NPD6050	Approved
0.7374	Intermediate Similarity	NPD8035	Phase 2
0.7374	Intermediate Similarity	NPD8034	Phase 2
0.7368	Intermediate Similarity	NPD6909	Approved
0.7368	Intermediate Similarity	NPD6908	Approved
0.7356	Intermediate Similarity	NPD4137	Phase 3
0.735	Intermediate Similarity	NPD8293	Discontinued
0.735	Intermediate Similarity	NPD7078	Approved
0.7333	Intermediate Similarity	NPD3703	Phase 2
0.732	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5133	Approved
0.7288	Intermediate Similarity	NPD6033	Approved
0.7288	Intermediate Similarity	NPD7736	Approved
0.7273	Intermediate Similarity	NPD4789	Approved
0.7273	Intermediate Similarity	NPD4691	Approved
0.7273	Intermediate Similarity	NPD5692	Phase 3
0.7253	Intermediate Similarity	NPD6117	Approved
0.7238	Intermediate Similarity	NPD5091	Approved
0.7238	Intermediate Similarity	NPD7632	Discontinued
0.7222	Intermediate Similarity	NPD5733	Approved
0.7222	Intermediate Similarity	NPD6926	Approved
0.7222	Intermediate Similarity	NPD6924	Approved
0.7217	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4623	Approved
0.7216	Intermediate Similarity	NPD4519	Discontinued
0.7204	Intermediate Similarity	NPD6929	Approved
0.7204	Intermediate Similarity	NPD7645	Phase 2
0.72	Intermediate Similarity	NPD5694	Approved
0.7193	Intermediate Similarity	NPD4522	Approved
0.7174	Intermediate Similarity	NPD6116	Phase 1
0.7159	Intermediate Similarity	NPD3699	Clinical (unspecified phase)

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