NPASS Compound

Structure

NPC471722 OpenBabel07101718332D 33 36 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 1.8781 3.1622 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 0.9000 2.9543 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 -0.8660 0.5000 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 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 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 0.5909 2.0032 0.0000 C 0 0 3 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 -2.5981 -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 -1.7321 -1.0000 0.0000 C 0 0 0 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 2 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 -0.3872 1.7953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 1 18 1 0 0 0 0 2 18 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 11 1 0 0 0 0 9 18 2 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 24 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 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 23 1 0 0 0 0 17 30 1 0 0 0 0 19 3 1 1 0 0 0 19 20 1 0 0 0 0 19 22 1 0 0 0 0 20 30 1 1 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 31 1 0 0 0 0 23 26 1 0 0 0 0 23 32 2 0 0 0 0 24 27 1 0 0 0 0 24 28 1 1 0 0 0 25 27 1 0 0 0 0 25 33 1 1 0 0 0 26 28 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	511.671
LogP:	5.95
LogD:	4.738
LogS:	-5.475
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.467
Synthetic Accessibility Score:	4.922
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.02
MDCK Permeability:	1.6600635717622936e-05
Pgp-inhibitor:	0.878
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	91.61790466308594%
Volume Distribution (VD):	0.861
Pgp-substrate:	2.675079584121704%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.327
CYP2C19-inhibitor:	0.139
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.298
CYP2C9-substrate:	0.194
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.693
CYP3A4-substrate:	0.734

ADMET: Excretion

Clearance (CL):	10.785
Half-life (T1/2):	0.059

ADMET: Toxicity

hERG Blockers:	0.142
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.472
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.523
Carcinogencity:	0.058
Eye Corrosion:	0.005
Eye Irritation:	0.019
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC471722

Natural Product ID:	NPC471722
*Common Name:**	3Beta,22-Dihydroxylanosta-8,24-Dien-11-One
IUPAC Name:	(3S,5R,10S,13R,14R,17R)-3-hydroxy-17-[(2S)-3-hydroxy-6-methylhept-5-en-2-yl]-4,4,10,13,14-pentamethyl-1,2,3,5,6,7,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
Synonyms:
Standard InCHIKey:	IJDKSGMUNLLABQ-BSBBLXHDSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-18(2)9-11-22(31)19(3)20-13-16-29(7)21-10-12-24-27(4,5)25(33)14-15-28(24,6)26(21)23(32)17-30(20,29)8/h9,19-20,22,24-25,31,33H,10-17H2,1-8H3/t19-,20+,22?,24-,25-,28-,29-,30+/m0/s1
SMILES:	CC(C1CCC2(C1(CC(=O)C3=C2CCC4C3(CCC(C4(C)C)O)C)C)C)C(CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105556
PubChem CID:	76321156
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
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[17049251]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[18387711]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24359303]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	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
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	81.2	%	PMID[557972]
NPT2	Others	Unspecified		Survival	=	94.0	%	PMID[557972]

☑ 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 NPC471722 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	160
0.1-0.2	1090
0.2-0.3	4875
0.3-0.4	13709
0.4-0.5	9190
0.5-0.6	6541
0.6-0.7	4637
0.7-0.8	2022
0.8-0.85	298
0.85-0.9	130
0.9-0.95	37
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC72133
0.9643	High Similarity	NPC86319
0.9643	High Similarity	NPC275740
0.9639	High Similarity	NPC475740
0.9529	High Similarity	NPC191684
0.9524	High Similarity	NPC131470
0.9524	High Similarity	NPC143767
0.9518	High Similarity	NPC474733
0.9518	High Similarity	NPC31564
0.9518	High Similarity	NPC474732
0.9518	High Similarity	NPC474778
0.9518	High Similarity	NPC222613
0.9518	High Similarity	NPC118648
0.9518	High Similarity	NPC475022
0.9518	High Similarity	NPC145879
0.9512	High Similarity	NPC473246
0.9412	High Similarity	NPC31985
0.9412	High Similarity	NPC1015
0.9405	High Similarity	NPC58063
0.9398	High Similarity	NPC470574
0.931	High Similarity	NPC69454
0.9302	High Similarity	NPC48010
0.9302	High Similarity	NPC183283
0.9294	High Similarity	NPC471724
0.9294	High Similarity	NPC328539
0.9286	High Similarity	NPC94755
0.9277	High Similarity	NPC85774
0.9277	High Similarity	NPC214043
0.9277	High Similarity	NPC221758
0.9277	High Similarity	NPC59453
0.9205	High Similarity	NPC166906
0.9205	High Similarity	NPC245972
0.9205	High Similarity	NPC196485
0.9195	High Similarity	NPC63748
0.9195	High Similarity	NPC272746
0.9195	High Similarity	NPC233116
0.9186	High Similarity	NPC268406
0.9186	High Similarity	NPC186688
0.9186	High Similarity	NPC119416
0.9186	High Similarity	NPC26959
0.9186	High Similarity	NPC309603
0.9186	High Similarity	NPC473999
0.9176	High Similarity	NPC159046
0.9176	High Similarity	NPC233836
0.9176	High Similarity	NPC187376
0.9167	High Similarity	NPC469948
0.9101	High Similarity	NPC259286
0.9101	High Similarity	NPC317586
0.9101	High Similarity	NPC470016
0.9091	High Similarity	NPC12722
0.9091	High Similarity	NPC475255
0.9091	High Similarity	NPC134826
0.908	High Similarity	NPC126993
0.908	High Similarity	NPC85173
0.907	High Similarity	NPC242864
0.9059	High Similarity	NPC51014
0.9059	High Similarity	NPC28252
0.9059	High Similarity	NPC55309
0.9048	High Similarity	NPC472265
0.9036	High Similarity	NPC151519
0.9	High Similarity	NPC96859
0.9	High Similarity	NPC305483
0.9	High Similarity	NPC249954
0.9	High Similarity	NPC328162
0.8989	High Similarity	NPC111015
0.8977	High Similarity	NPC473998
0.8977	High Similarity	NPC475806
0.8977	High Similarity	NPC168027
0.8977	High Similarity	NPC185936
0.8966	High Similarity	NPC102414
0.8966	High Similarity	NPC474245
0.8966	High Similarity	NPC32830
0.8966	High Similarity	NPC84271
0.8966	High Similarity	NPC77168
0.8953	High Similarity	NPC136548
0.8953	High Similarity	NPC142361
0.8953	High Similarity	NPC474684
0.8953	High Similarity	NPC141292
0.8941	High Similarity	NPC474083
0.8941	High Similarity	NPC197823
0.8929	High Similarity	NPC278648
0.8929	High Similarity	NPC476082
0.8901	High Similarity	NPC108078
0.8901	High Similarity	NPC320306
0.8889	High Similarity	NPC271195
0.8876	High Similarity	NPC472930
0.8876	High Similarity	NPC250575
0.8851	High Similarity	NPC474677
0.8851	High Similarity	NPC193360
0.8851	High Similarity	NPC292491
0.8851	High Similarity	NPC53911
0.8851	High Similarity	NPC310752
0.8851	High Similarity	NPC328313
0.8837	High Similarity	NPC155011
0.8824	High Similarity	NPC161423
0.8824	High Similarity	NPC82902
0.8824	High Similarity	NPC237712
0.8824	High Similarity	NPC329043
0.8824	High Similarity	NPC321187
0.8824	High Similarity	NPC33913
0.8824	High Similarity	NPC227064
0.8824	High Similarity	NPC58841
0.8795	High Similarity	NPC2482
0.8791	High Similarity	NPC117133
0.878	High Similarity	NPC275910
0.8778	High Similarity	NPC8993
0.8764	High Similarity	NPC155304
0.8764	High Similarity	NPC131872
0.8764	High Similarity	NPC297265
0.8764	High Similarity	NPC26888
0.875	High Similarity	NPC474704
0.875	High Similarity	NPC477943
0.875	High Similarity	NPC76879
0.875	High Similarity	NPC475921
0.8736	High Similarity	NPC475772
0.8736	High Similarity	NPC93778
0.8736	High Similarity	NPC138756
0.8723	High Similarity	NPC473424
0.8721	High Similarity	NPC471224
0.8721	High Similarity	NPC474218
0.8721	High Similarity	NPC202868
0.871	High Similarity	NPC327431
0.871	High Similarity	NPC316964
0.8696	High Similarity	NPC43747
0.869	High Similarity	NPC136150
0.8681	High Similarity	NPC127063
0.8681	High Similarity	NPC173875
0.8681	High Similarity	NPC174948
0.8681	High Similarity	NPC472932
0.8681	High Similarity	NPC200702
0.8681	High Similarity	NPC318282
0.8681	High Similarity	NPC473170
0.8681	High Similarity	NPC469995
0.8675	High Similarity	NPC472490
0.8667	High Similarity	NPC109305
0.8667	High Similarity	NPC474736
0.8659	High Similarity	NPC214570
0.8659	High Similarity	NPC197659
0.8652	High Similarity	NPC69622
0.8652	High Similarity	NPC148414
0.8652	High Similarity	NPC469400
0.8652	High Similarity	NPC175628
0.8652	High Similarity	NPC111585
0.8636	High Similarity	NPC206060
0.8636	High Similarity	NPC472802
0.8621	High Similarity	NPC327115
0.8621	High Similarity	NPC20688
0.8621	High Similarity	NPC158393
0.8621	High Similarity	NPC472974
0.8621	High Similarity	NPC469994
0.8621	High Similarity	NPC89077
0.8602	High Similarity	NPC114274
0.8602	High Similarity	NPC103051
0.8588	High Similarity	NPC48362
0.8588	High Similarity	NPC260956
0.8587	High Similarity	NPC328371
0.8587	High Similarity	NPC192428
0.8587	High Similarity	NPC472941
0.8587	High Similarity	NPC456
0.8587	High Similarity	NPC173272
0.8587	High Similarity	NPC95565
0.8571	High Similarity	NPC472478
0.8571	High Similarity	NPC23170
0.8571	High Similarity	NPC474690
0.8571	High Similarity	NPC469406
0.8556	High Similarity	NPC23434
0.8556	High Similarity	NPC19114
0.8556	High Similarity	NPC212301
0.8556	High Similarity	NPC189520
0.8556	High Similarity	NPC86266
0.8556	High Similarity	NPC110657
0.8539	High Similarity	NPC128496
0.8539	High Similarity	NPC472970
0.8539	High Similarity	NPC250592
0.8539	High Similarity	NPC474889
0.8539	High Similarity	NPC77263
0.8539	High Similarity	NPC214387
0.8539	High Similarity	NPC472971
0.8537	High Similarity	NPC202642
0.8537	High Similarity	NPC73875
0.8537	High Similarity	NPC46160
0.8526	High Similarity	NPC293753
0.8526	High Similarity	NPC234892
0.8523	High Similarity	NPC90652
0.8523	High Similarity	NPC317590
0.8523	High Similarity	NPC73064
0.8523	High Similarity	NPC99909
0.8511	High Similarity	NPC154072
0.8511	High Similarity	NPC112167
0.8506	High Similarity	NPC76518
0.8506	High Similarity	NPC133954
0.8495	Intermediate Similarity	NPC18509
0.8495	Intermediate Similarity	NPC190554
0.8488	Intermediate Similarity	NPC472743
0.8488	Intermediate Similarity	NPC475726
0.8488	Intermediate Similarity	NPC168188
0.8488	Intermediate Similarity	NPC64600
0.8488	Intermediate Similarity	NPC470015
0.8478	Intermediate Similarity	NPC48330
0.8478	Intermediate Similarity	NPC297199

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 NPC471722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1441
0.2-0.3	4065
0.3-0.4	2440
0.4-0.5	589
0.5-0.6	161
0.6-0.7	137
0.7-0.8	145
0.8-0.85	19
0.85-0.9	7
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9412	High Similarity	NPD5328	Approved
0.9286	High Similarity	NPD3618	Phase 1
0.9277	High Similarity	NPD4786	Approved
0.9195	High Similarity	NPD6079	Approved
0.9036	High Similarity	NPD3667	Approved
0.8876	High Similarity	NPD4202	Approved
0.8837	High Similarity	NPD5279	Phase 3
0.8824	High Similarity	NPD3133	Approved
0.8824	High Similarity	NPD3665	Phase 1
0.8824	High Similarity	NPD3666	Approved
0.8587	High Similarity	NPD5221	Approved
0.8587	High Similarity	NPD4697	Phase 3
0.8587	High Similarity	NPD5220	Clinical (unspecified phase)
0.8587	High Similarity	NPD5222	Approved
0.8495	Intermediate Similarity	NPD5173	Approved
0.8495	Intermediate Similarity	NPD4755	Approved
0.8372	Intermediate Similarity	NPD4223	Phase 3
0.8372	Intermediate Similarity	NPD4221	Approved
0.8352	Intermediate Similarity	NPD7515	Phase 2
0.8333	Intermediate Similarity	NPD4753	Phase 2
0.8316	Intermediate Similarity	NPD4700	Approved
0.8316	Intermediate Similarity	NPD4696	Approved
0.8316	Intermediate Similarity	NPD5286	Approved
0.8316	Intermediate Similarity	NPD5285	Approved
0.8295	Intermediate Similarity	NPD5329	Approved
0.8261	Intermediate Similarity	NPD6399	Phase 3
0.8229	Intermediate Similarity	NPD5223	Approved
0.8202	Intermediate Similarity	NPD4694	Approved
0.8202	Intermediate Similarity	NPD5280	Approved
0.8202	Intermediate Similarity	NPD5690	Phase 2
0.8193	Intermediate Similarity	NPD6942	Approved
0.8193	Intermediate Similarity	NPD7339	Approved
0.8182	Intermediate Similarity	NPD4197	Approved
0.8182	Intermediate Similarity	NPD3668	Phase 3
0.8144	Intermediate Similarity	NPD5224	Approved
0.8144	Intermediate Similarity	NPD5226	Approved
0.8144	Intermediate Similarity	NPD4633	Approved
0.8144	Intermediate Similarity	NPD5225	Approved
0.8144	Intermediate Similarity	NPD5211	Phase 2
0.809	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7128	Approved
0.8081	Intermediate Similarity	NPD6675	Approved
0.8081	Intermediate Similarity	NPD6402	Approved
0.8081	Intermediate Similarity	NPD5739	Approved
0.8061	Intermediate Similarity	NPD5174	Approved
0.8061	Intermediate Similarity	NPD4754	Approved
0.8061	Intermediate Similarity	NPD5175	Approved
0.8	Intermediate Similarity	NPD4138	Approved
0.8	Intermediate Similarity	NPD4688	Approved
0.8	Intermediate Similarity	NPD5205	Approved
0.8	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7521	Approved
0.8	Intermediate Similarity	NPD4689	Approved
0.8	Intermediate Similarity	NPD4693	Phase 3
0.8	Intermediate Similarity	NPD7146	Approved
0.8	Intermediate Similarity	NPD6684	Approved
0.8	Intermediate Similarity	NPD4690	Approved
0.8	Intermediate Similarity	NPD5330	Approved
0.8	Intermediate Similarity	NPD6409	Approved
0.8	Intermediate Similarity	NPD7334	Approved
0.798	Intermediate Similarity	NPD5141	Approved
0.7979	Intermediate Similarity	NPD7748	Approved
0.7931	Intermediate Similarity	NPD7525	Registered
0.7921	Intermediate Similarity	NPD7320	Approved
0.7921	Intermediate Similarity	NPD6899	Approved
0.7921	Intermediate Similarity	NPD6881	Approved
0.7917	Intermediate Similarity	NPD6083	Phase 2
0.7917	Intermediate Similarity	NPD6084	Phase 2
0.7907	Intermediate Similarity	NPD3617	Approved
0.79	Intermediate Similarity	NPD4768	Approved
0.79	Intermediate Similarity	NPD4767	Approved
0.7895	Intermediate Similarity	NPD5695	Phase 3
0.7895	Intermediate Similarity	NPD4629	Approved
0.7895	Intermediate Similarity	NPD5210	Approved
0.7882	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD4788	Approved
0.7857	Intermediate Similarity	NPD5733	Approved
0.7843	Intermediate Similarity	NPD6373	Approved
0.7843	Intermediate Similarity	NPD6372	Approved
0.7826	Intermediate Similarity	NPD6672	Approved
0.7826	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5737	Approved
0.7826	Intermediate Similarity	NPD6903	Approved
0.7822	Intermediate Similarity	NPD5701	Approved
0.7822	Intermediate Similarity	NPD5697	Approved
0.7767	Intermediate Similarity	NPD7290	Approved
0.7767	Intermediate Similarity	NPD6883	Approved
0.7767	Intermediate Similarity	NPD7102	Approved
0.7766	Intermediate Similarity	NPD5284	Approved
0.7766	Intermediate Similarity	NPD5281	Approved
0.7745	Intermediate Similarity	NPD6011	Approved
0.7745	Intermediate Similarity	NPD5168	Approved
0.7745	Intermediate Similarity	NPD4730	Approved
0.7745	Intermediate Similarity	NPD4729	Approved
0.7745	Intermediate Similarity	NPD5128	Approved
0.7732	Intermediate Similarity	NPD7902	Approved
0.7727	Intermediate Similarity	NPD4695	Discontinued
0.7711	Intermediate Similarity	NPD4747	Approved
0.7692	Intermediate Similarity	NPD6869	Approved
0.7692	Intermediate Similarity	NPD6617	Approved
0.7692	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6649	Approved
0.7692	Intermediate Similarity	NPD8130	Phase 1
0.7692	Intermediate Similarity	NPD6650	Approved
0.7692	Intermediate Similarity	NPD6847	Approved
0.767	Intermediate Similarity	NPD6014	Approved
0.767	Intermediate Similarity	NPD6013	Approved
0.767	Intermediate Similarity	NPD6012	Approved
0.766	Intermediate Similarity	NPD4096	Approved
0.7653	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD4687	Approved
0.764	Intermediate Similarity	NPD4692	Approved
0.764	Intermediate Similarity	NPD4139	Approved
0.7634	Intermediate Similarity	NPD4518	Approved
0.7619	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6882	Approved
0.7619	Intermediate Similarity	NPD5276	Approved
0.7619	Intermediate Similarity	NPD8297	Approved
0.7619	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4195	Approved
0.7596	Intermediate Similarity	NPD5247	Approved
0.7596	Intermediate Similarity	NPD5169	Approved
0.7596	Intermediate Similarity	NPD5250	Approved
0.7596	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD5135	Approved
0.7596	Intermediate Similarity	NPD4634	Approved
0.7596	Intermediate Similarity	NPD5249	Phase 3
0.7596	Intermediate Similarity	NPD5248	Approved
0.7596	Intermediate Similarity	NPD5251	Approved
0.759	Intermediate Similarity	NPD4137	Phase 3
0.7576	Intermediate Similarity	NPD7640	Approved
0.7576	Intermediate Similarity	NPD7639	Approved
0.7528	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4748	Discontinued
0.7526	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5215	Approved
0.7524	Intermediate Similarity	NPD5217	Approved
0.7524	Intermediate Similarity	NPD5127	Approved
0.7524	Intermediate Similarity	NPD5216	Approved
0.75	Intermediate Similarity	NPD5133	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD4691	Approved
0.7475	Intermediate Similarity	NPD5696	Approved
0.7442	Intermediate Similarity	NPD6926	Approved
0.7442	Intermediate Similarity	NPD6924	Approved
0.7423	Intermediate Similarity	NPD7900	Approved
0.7423	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4519	Discontinued
0.7419	Intermediate Similarity	NPD4623	Approved
0.7416	Intermediate Similarity	NPD7645	Phase 2
0.7407	Intermediate Similarity	NPD6868	Approved
0.7396	Intermediate Similarity	NPD8035	Phase 2
0.7396	Intermediate Similarity	NPD8034	Phase 2
0.7396	Intermediate Similarity	NPD6050	Approved
0.7383	Intermediate Similarity	NPD4632	Approved
0.7381	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6008	Approved
0.7368	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6904	Approved
0.7368	Intermediate Similarity	NPD6673	Approved
0.7368	Intermediate Similarity	NPD6080	Approved
0.7315	Intermediate Similarity	NPD5167	Approved
0.7308	Intermediate Similarity	NPD6412	Phase 2
0.73	Intermediate Similarity	NPD5290	Discontinued
0.7292	Intermediate Similarity	NPD5207	Approved
0.7292	Intermediate Similarity	NPD5692	Phase 3
0.7273	Intermediate Similarity	NPD6117	Approved
0.7273	Intermediate Similarity	NPD6335	Approved
0.7273	Intermediate Similarity	NPD6933	Approved
0.7263	Intermediate Similarity	NPD5208	Approved
0.7248	Intermediate Similarity	NPD6274	Approved
0.7245	Intermediate Similarity	NPD6001	Approved
0.7241	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4784	Approved
0.7241	Intermediate Similarity	NPD4785	Approved
0.7241	Intermediate Similarity	NPD4058	Approved
0.7234	Intermediate Similarity	NPD6098	Approved
0.7216	Intermediate Similarity	NPD6411	Approved
0.7216	Intermediate Similarity	NPD5694	Approved
0.7209	Intermediate Similarity	NPD4243	Approved
0.7209	Intermediate Similarity	NPD7152	Approved
0.7209	Intermediate Similarity	NPD7150	Approved
0.7209	Intermediate Similarity	NPD7151	Approved
0.7207	Intermediate Similarity	NPD7101	Approved
0.7207	Intermediate Similarity	NPD7100	Approved
0.7191	Intermediate Similarity	NPD6116	Phase 1
0.7182	Intermediate Similarity	NPD6317	Approved
0.7182	Intermediate Similarity	NPD6009	Approved
0.7176	Intermediate Similarity	NPD6922	Approved
0.7176	Intermediate Similarity	NPD6923	Approved
0.7159	Intermediate Similarity	NPD3703	Phase 2
0.7158	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3573	Approved
0.7143	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7117	Intermediate Similarity	NPD6314	Approved
0.7117	Intermediate Similarity	NPD6313	Approved
0.7111	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6115	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