NPASS Compound

Structure

NPC471724 OpenBabel07101718332D 33 36 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 -2.2382 -2.4680 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 2.9641 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 0.8660 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 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 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 -0.9511 0.3090 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 -0.9000 -3.9543 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 1 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 1.7321 -0.0000 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 -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 3 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 1 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 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 -2.5472 -3.4190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 -2.7953 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 1 18 2 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 10 1 0 0 0 0 9 22 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 29 1 0 0 0 0 17 23 1 0 0 0 0 17 24 1 0 0 0 0 18 23 1 0 0 0 0 19 3 1 1 0 0 0 19 20 1 0 0 0 0 19 24 1 0 0 0 0 20 29 1 1 0 0 0 21 22 2 0 0 0 0 21 28 1 0 0 0 0 22 30 1 0 0 0 0 23 31 2 0 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 28 1 1 0 0 0 26 27 1 0 0 0 0 26 33 1 1 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:	456.36
Volume:	511.671
LogP:	4.967
LogD:	4.509
LogS:	-5.012
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.361
Synthetic Accessibility Score:	4.891
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.99
MDCK Permeability:	1.4634072613262106e-05
Pgp-inhibitor:	0.834
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.549
30% Bioavailability (F30%):	0.799

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	89.38069152832031%
Volume Distribution (VD):	0.84
Pgp-substrate:	1.6236345767974854%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.566
CYP2C19-inhibitor:	0.131
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.327
CYP2C9-substrate:	0.344
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.318
CYP3A4-inhibitor:	0.557
CYP3A4-substrate:	0.815

ADMET: Excretion

Clearance (CL):	7.582
Half-life (T1/2):	0.083

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.358
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.76
Carcinogencity:	0.04
Eye Corrosion:	0.12
Eye Irritation:	0.178
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC471724

Natural Product ID:	NPC471724
*Common Name:**	3Beta,22-Dihydroxy-5Alpha-Lanosta-8,25-Dien-24-One
IUPAC Name:	(6S)-5-hydroxy-6-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-1-en-3-one
Synonyms:
Standard InCHIKey:	NRZPHWXZFDFOQN-GJLUZCMASA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-18(2)23(31)17-24(32)19(3)20-11-15-30(8)22-9-10-25-27(4,5)26(33)13-14-28(25,6)21(22)12-16-29(20,30)7/h19-20,24-26,32-33H,1,9-17H2,2-8H3/t19-,20+,24?,25-,26-,28+,29+,30-/m0/s1
SMILES:	CC(C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C)C(CC(=O)C(=C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105558
PubChem CID:	76310204
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
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	9900.0	nM	PMID[570131]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[570131]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[570131]

☑ 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 NPC471724 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	1258
0.2-0.3	5613
0.3-0.4	14152
0.4-0.5	8582
0.5-0.6	6403
0.6-0.7	4602
0.7-0.8	1600
0.8-0.85	250
0.85-0.9	60
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9518	High Similarity	NPC72133
0.9302	High Similarity	NPC191684
0.9294	High Similarity	NPC471722
0.9294	High Similarity	NPC131470
0.9294	High Similarity	NPC143767
0.9186	High Similarity	NPC275740
0.9186	High Similarity	NPC86319
0.908	High Similarity	NPC183283
0.9059	High Similarity	NPC28252
0.9059	High Similarity	NPC94755
0.9059	High Similarity	NPC55309
0.9048	High Similarity	NPC473246
0.8977	High Similarity	NPC63748
0.8977	High Similarity	NPC233116
0.8977	High Similarity	NPC272746
0.8953	High Similarity	NPC159046
0.8953	High Similarity	NPC233836
0.8953	High Similarity	NPC187376
0.8953	High Similarity	NPC475740
0.8941	High Similarity	NPC470574
0.8929	High Similarity	NPC471036
0.8929	High Similarity	NPC291320
0.8902	High Similarity	NPC472490
0.8876	High Similarity	NPC69454
0.8864	High Similarity	NPC85173
0.8864	High Similarity	NPC126993
0.8851	High Similarity	NPC242864
0.8851	High Similarity	NPC53911
0.8851	High Similarity	NPC328313
0.8851	High Similarity	NPC328539
0.8837	High Similarity	NPC474733
0.8837	High Similarity	NPC474778
0.8837	High Similarity	NPC145879
0.8837	High Similarity	NPC222613
0.8837	High Similarity	NPC475022
0.8837	High Similarity	NPC474732
0.8837	High Similarity	NPC118648
0.8837	High Similarity	NPC31564
0.8824	High Similarity	NPC221758
0.8824	High Similarity	NPC85774
0.8824	High Similarity	NPC214043
0.8824	High Similarity	NPC59453
0.8778	High Similarity	NPC166906
0.875	High Similarity	NPC84271
0.875	High Similarity	NPC473999
0.875	High Similarity	NPC102414
0.875	High Similarity	NPC119416
0.875	High Similarity	NPC472970
0.875	High Similarity	NPC309603
0.875	High Similarity	NPC1015
0.875	High Similarity	NPC472971
0.875	High Similarity	NPC472489
0.875	High Similarity	NPC77168
0.875	High Similarity	NPC31985
0.8736	High Similarity	NPC58063
0.8736	High Similarity	NPC474684
0.8736	High Similarity	NPC138756
0.8736	High Similarity	NPC142361
0.8721	High Similarity	NPC190704
0.8721	High Similarity	NPC474083
0.8721	High Similarity	NPC471034
0.8721	High Similarity	NPC76518
0.8681	High Similarity	NPC470016
0.8681	High Similarity	NPC317586
0.8681	High Similarity	NPC259286
0.8667	High Similarity	NPC475255
0.8667	High Similarity	NPC134826
0.8652	High Similarity	NPC48010
0.8652	High Similarity	NPC469400
0.8636	High Similarity	NPC193360
0.8621	High Similarity	NPC472491
0.8621	High Similarity	NPC51014
0.8621	High Similarity	NPC472494
0.8617	High Similarity	NPC473514
0.8605	High Similarity	NPC472265
0.8605	High Similarity	NPC82902
0.8588	High Similarity	NPC151519
0.8587	High Similarity	NPC120708
0.8587	High Similarity	NPC305483
0.8587	High Similarity	NPC328162
0.8587	High Similarity	NPC249954
0.8587	High Similarity	NPC96859
0.8571	High Similarity	NPC472478
0.8571	High Similarity	NPC245972
0.8571	High Similarity	NPC111015
0.8571	High Similarity	NPC196485
0.8556	High Similarity	NPC185936
0.8556	High Similarity	NPC473998
0.8556	High Similarity	NPC168027
0.8556	High Similarity	NPC297265
0.8556	High Similarity	NPC23434
0.8556	High Similarity	NPC475806
0.8539	High Similarity	NPC32830
0.8539	High Similarity	NPC474245
0.8539	High Similarity	NPC26959
0.8539	High Similarity	NPC474704
0.8539	High Similarity	NPC268406
0.8539	High Similarity	NPC186688
0.8539	High Similarity	NPC474889
0.8539	High Similarity	NPC475921
0.8537	High Similarity	NPC73875
0.8523	High Similarity	NPC475772
0.8523	High Similarity	NPC57469
0.8523	High Similarity	NPC93778
0.8523	High Similarity	NPC165895
0.8523	High Similarity	NPC141292
0.8523	High Similarity	NPC136548
0.8523	High Similarity	NPC259009
0.8523	High Similarity	NPC96496
0.8506	High Similarity	NPC474218
0.8506	High Similarity	NPC471224
0.8506	High Similarity	NPC197823
0.8506	High Similarity	NPC102292
0.8506	High Similarity	NPC469948
0.8495	Intermediate Similarity	NPC320306
0.8495	Intermediate Similarity	NPC108078
0.8488	Intermediate Similarity	NPC278648
0.8488	Intermediate Similarity	NPC472743
0.8488	Intermediate Similarity	NPC475726
0.8488	Intermediate Similarity	NPC476082
0.8478	Intermediate Similarity	NPC271195
0.8471	Intermediate Similarity	NPC116797
0.8462	Intermediate Similarity	NPC472930
0.8462	Intermediate Similarity	NPC12722
0.8462	Intermediate Similarity	NPC474807
0.8462	Intermediate Similarity	NPC250575
0.8444	Intermediate Similarity	NPC111585
0.8444	Intermediate Similarity	NPC175628
0.8444	Intermediate Similarity	NPC148414
0.8444	Intermediate Similarity	NPC136801
0.8434	Intermediate Similarity	NPC214570
0.8427	Intermediate Similarity	NPC472739
0.8427	Intermediate Similarity	NPC292491
0.8427	Intermediate Similarity	NPC310752
0.8427	Intermediate Similarity	NPC474677
0.8421	Intermediate Similarity	NPC472924
0.8415	Intermediate Similarity	NPC121744
0.8415	Intermediate Similarity	NPC322353
0.8415	Intermediate Similarity	NPC118508
0.8409	Intermediate Similarity	NPC158393
0.8409	Intermediate Similarity	NPC155011
0.8409	Intermediate Similarity	NPC98236
0.8409	Intermediate Similarity	NPC472488
0.8409	Intermediate Similarity	NPC89077
0.8409	Intermediate Similarity	NPC269396
0.8409	Intermediate Similarity	NPC469994
0.8404	Intermediate Similarity	NPC147954
0.8404	Intermediate Similarity	NPC103051
0.8391	Intermediate Similarity	NPC329043
0.8391	Intermediate Similarity	NPC474482
0.8391	Intermediate Similarity	NPC237712
0.8391	Intermediate Similarity	NPC33913
0.8391	Intermediate Similarity	NPC321187
0.8391	Intermediate Similarity	NPC161423
0.8391	Intermediate Similarity	NPC58841
0.8391	Intermediate Similarity	NPC227064
0.8391	Intermediate Similarity	NPC146683
0.8391	Intermediate Similarity	NPC475745
0.8387	Intermediate Similarity	NPC472941
0.8387	Intermediate Similarity	NPC456
0.8387	Intermediate Similarity	NPC117133
0.8372	Intermediate Similarity	NPC110780
0.8372	Intermediate Similarity	NPC48362
0.837	Intermediate Similarity	NPC469406
0.837	Intermediate Similarity	NPC8993
0.8367	Intermediate Similarity	NPC472925
0.8353	Intermediate Similarity	NPC164999
0.8352	Intermediate Similarity	NPC131872
0.8352	Intermediate Similarity	NPC189520
0.8352	Intermediate Similarity	NPC212301
0.8352	Intermediate Similarity	NPC86266
0.8352	Intermediate Similarity	NPC110657
0.8352	Intermediate Similarity	NPC26888
0.8352	Intermediate Similarity	NPC155304
0.8351	Intermediate Similarity	NPC96268
0.8333	Intermediate Similarity	NPC54689
0.8333	Intermediate Similarity	NPC477943
0.8333	Intermediate Similarity	NPC293753
0.8333	Intermediate Similarity	NPC472475
0.8333	Intermediate Similarity	NPC472477
0.8333	Intermediate Similarity	NPC76879
0.8333	Intermediate Similarity	NPC275910
0.8333	Intermediate Similarity	NPC473424
0.8333	Intermediate Similarity	NPC214387
0.8333	Intermediate Similarity	NPC69627
0.8333	Intermediate Similarity	NPC178852
0.8316	Intermediate Similarity	NPC316964
0.8316	Intermediate Similarity	NPC110149
0.8316	Intermediate Similarity	NPC327431
0.8315	Intermediate Similarity	NPC317590
0.8315	Intermediate Similarity	NPC472481
0.8315	Intermediate Similarity	NPC472493
0.8315	Intermediate Similarity	NPC99909
0.8315	Intermediate Similarity	NPC472482
0.8315	Intermediate Similarity	NPC90652
0.8315	Intermediate Similarity	NPC472484
0.8313	Intermediate Similarity	NPC202642
0.8313	Intermediate Similarity	NPC46160
0.8298	Intermediate Similarity	NPC43747
0.8295	Intermediate Similarity	NPC292553

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 NPC471724 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1662
0.2-0.3	4218
0.3-0.4	2172
0.4-0.5	496
0.5-0.6	163
0.6-0.7	153
0.7-0.8	125
0.8-0.85	11
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8977	High Similarity	NPD6079	Approved
0.8966	High Similarity	NPD5328	Approved
0.8837	High Similarity	NPD3618	Phase 1
0.8824	High Similarity	NPD4786	Approved
0.8588	High Similarity	NPD3667	Approved
0.8462	Intermediate Similarity	NPD4202	Approved
0.8409	Intermediate Similarity	NPD5279	Phase 3
0.8391	Intermediate Similarity	NPD3133	Approved
0.8391	Intermediate Similarity	NPD3665	Phase 1
0.8391	Intermediate Similarity	NPD3666	Approved
0.8387	Intermediate Similarity	NPD5222	Approved
0.8387	Intermediate Similarity	NPD5221	Approved
0.8387	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD5173	Approved
0.8202	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8191	Intermediate Similarity	NPD4697	Phase 3
0.8125	Intermediate Similarity	NPD5285	Approved
0.8125	Intermediate Similarity	NPD4696	Approved
0.8125	Intermediate Similarity	NPD5286	Approved
0.8105	Intermediate Similarity	NPD4755	Approved
0.809	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD4788	Approved
0.8041	Intermediate Similarity	NPD5223	Approved
0.8	Intermediate Similarity	NPD5690	Phase 2
0.7959	Intermediate Similarity	NPD5224	Approved
0.7959	Intermediate Similarity	NPD4633	Approved
0.7959	Intermediate Similarity	NPD5225	Approved
0.7959	Intermediate Similarity	NPD5226	Approved
0.7959	Intermediate Similarity	NPD5211	Phase 2
0.7957	Intermediate Similarity	NPD7515	Phase 2
0.7955	Intermediate Similarity	NPD4223	Phase 3
0.7955	Intermediate Similarity	NPD4221	Approved
0.7938	Intermediate Similarity	NPD4700	Approved
0.7935	Intermediate Similarity	NPD4753	Phase 2
0.7889	Intermediate Similarity	NPD5329	Approved
0.7879	Intermediate Similarity	NPD5174	Approved
0.7879	Intermediate Similarity	NPD5175	Approved
0.7872	Intermediate Similarity	NPD6399	Phase 3
0.7802	Intermediate Similarity	NPD5280	Approved
0.7802	Intermediate Similarity	NPD4694	Approved
0.78	Intermediate Similarity	NPD5141	Approved
0.7778	Intermediate Similarity	NPD4197	Approved
0.7778	Intermediate Similarity	NPD3668	Phase 3
0.7767	Intermediate Similarity	NPD4634	Approved
0.7765	Intermediate Similarity	NPD7339	Approved
0.7765	Intermediate Similarity	NPD6942	Approved
0.7745	Intermediate Similarity	NPD6881	Approved
0.7745	Intermediate Similarity	NPD6899	Approved
0.7727	Intermediate Similarity	NPD7525	Registered
0.7723	Intermediate Similarity	NPD6675	Approved
0.7723	Intermediate Similarity	NPD7128	Approved
0.7723	Intermediate Similarity	NPD6402	Approved
0.7723	Intermediate Similarity	NPD5739	Approved
0.7708	Intermediate Similarity	NPD5210	Approved
0.7708	Intermediate Similarity	NPD4629	Approved
0.7701	Intermediate Similarity	NPD3617	Approved
0.77	Intermediate Similarity	NPD4754	Approved
0.7647	Intermediate Similarity	NPD5697	Approved
0.764	Intermediate Similarity	NPD4139	Approved
0.764	Intermediate Similarity	NPD4692	Approved
0.7619	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6409	Approved
0.7609	Intermediate Similarity	NPD4689	Approved
0.7609	Intermediate Similarity	NPD4688	Approved
0.7609	Intermediate Similarity	NPD5330	Approved
0.7609	Intermediate Similarity	NPD4693	Phase 3
0.7609	Intermediate Similarity	NPD6684	Approved
0.7609	Intermediate Similarity	NPD4690	Approved
0.7609	Intermediate Similarity	NPD7521	Approved
0.7609	Intermediate Similarity	NPD7334	Approved
0.7609	Intermediate Similarity	NPD5205	Approved
0.7609	Intermediate Similarity	NPD4138	Approved
0.7609	Intermediate Similarity	NPD7146	Approved
0.7604	Intermediate Similarity	NPD7748	Approved
0.7596	Intermediate Similarity	NPD7290	Approved
0.7596	Intermediate Similarity	NPD7102	Approved
0.7596	Intermediate Similarity	NPD6883	Approved
0.7573	Intermediate Similarity	NPD6011	Approved
0.7573	Intermediate Similarity	NPD5168	Approved
0.7573	Intermediate Similarity	NPD4729	Approved
0.7573	Intermediate Similarity	NPD5128	Approved
0.7573	Intermediate Similarity	NPD7320	Approved
0.7573	Intermediate Similarity	NPD4730	Approved
0.7551	Intermediate Similarity	NPD6083	Phase 2
0.7551	Intermediate Similarity	NPD6084	Phase 2
0.7549	Intermediate Similarity	NPD4768	Approved
0.7549	Intermediate Similarity	NPD4767	Approved
0.7526	Intermediate Similarity	NPD5695	Phase 3
0.7524	Intermediate Similarity	NPD8130	Phase 1
0.7524	Intermediate Similarity	NPD6617	Approved
0.7524	Intermediate Similarity	NPD6650	Approved
0.7524	Intermediate Similarity	NPD6869	Approved
0.7524	Intermediate Similarity	NPD6649	Approved
0.7524	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7476	Intermediate Similarity	NPD5701	Approved
0.7471	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD8297	Approved
0.7453	Intermediate Similarity	NPD6882	Approved
0.7447	Intermediate Similarity	NPD6903	Approved
0.7447	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5737	Approved
0.7447	Intermediate Similarity	NPD6672	Approved
0.7442	Intermediate Similarity	NPD5733	Approved
0.7429	Intermediate Similarity	NPD5250	Approved
0.7429	Intermediate Similarity	NPD5251	Approved
0.7429	Intermediate Similarity	NPD5169	Approved
0.7429	Intermediate Similarity	NPD5248	Approved
0.7429	Intermediate Similarity	NPD5247	Approved
0.7429	Intermediate Similarity	NPD5249	Phase 3
0.7429	Intermediate Similarity	NPD5135	Approved
0.7429	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4195	Approved
0.7396	Intermediate Similarity	NPD5281	Approved
0.7396	Intermediate Similarity	NPD8034	Phase 2
0.7396	Intermediate Similarity	NPD8035	Phase 2
0.7396	Intermediate Similarity	NPD5284	Approved
0.7381	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7902	Approved
0.7358	Intermediate Similarity	NPD5127	Approved
0.7358	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5217	Approved
0.7358	Intermediate Similarity	NPD5216	Approved
0.7358	Intermediate Similarity	NPD5215	Approved
0.7333	Intermediate Similarity	NPD4748	Discontinued
0.7333	Intermediate Similarity	NPD4695	Discontinued
0.73	Intermediate Similarity	NPD7638	Approved
0.7297	Intermediate Similarity	NPD6054	Approved
0.7294	Intermediate Similarity	NPD4747	Approved
0.7294	Intermediate Similarity	NPD4691	Approved
0.7292	Intermediate Similarity	NPD4096	Approved
0.7273	Intermediate Similarity	NPD6117	Approved
0.7248	Intermediate Similarity	NPD6868	Approved
0.7241	Intermediate Similarity	NPD4687	Approved
0.7241	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7640	Approved
0.7228	Intermediate Similarity	NPD7639	Approved
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7222	Intermediate Similarity	NPD4632	Approved
0.7216	Intermediate Similarity	NPD6411	Approved
0.7209	Intermediate Similarity	NPD5276	Approved
0.7191	Intermediate Similarity	NPD6116	Phase 1
0.7176	Intermediate Similarity	NPD4137	Phase 3
0.7172	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6370	Approved
0.7159	Intermediate Similarity	NPD3703	Phase 2
0.7156	Intermediate Similarity	NPD5167	Approved
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD5133	Approved
0.7129	Intermediate Similarity	NPD5290	Discontinued
0.7129	Intermediate Similarity	NPD5696	Approved
0.7117	Intermediate Similarity	NPD6335	Approved
0.7111	Intermediate Similarity	NPD6114	Approved
0.7111	Intermediate Similarity	NPD6697	Approved
0.7111	Intermediate Similarity	NPD6118	Approved
0.7111	Intermediate Similarity	NPD6115	Approved
0.7108	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4244	Approved
0.7093	Intermediate Similarity	NPD4245	Approved
0.7093	Intermediate Similarity	NPD4789	Approved
0.7091	Intermediate Similarity	NPD6274	Approved
0.7083	Intermediate Similarity	NPD4518	Approved
0.708	Intermediate Similarity	NPD6015	Approved
0.708	Intermediate Similarity	NPD6016	Approved
0.7071	Intermediate Similarity	NPD7900	Approved
0.7071	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5360	Phase 3
0.7059	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7100	Approved
0.7054	Intermediate Similarity	NPD7101	Approved
0.7053	Intermediate Similarity	NPD6098	Approved
0.7053	Intermediate Similarity	NPD4623	Approved
0.7053	Intermediate Similarity	NPD4519	Discontinued
0.7045	Intermediate Similarity	NPD4058	Approved
0.7045	Intermediate Similarity	NPD6924	Approved
0.7045	Intermediate Similarity	NPD6926	Approved
0.7043	Intermediate Similarity	NPD7492	Approved
0.7041	Intermediate Similarity	NPD6050	Approved
0.7027	Intermediate Similarity	NPD6317	Approved
0.7027	Intermediate Similarity	NPD6009	Approved
0.7018	Intermediate Similarity	NPD5988	Approved
0.7011	Intermediate Similarity	NPD4243	Approved
0.701	Intermediate Similarity	NPD6673	Approved
0.701	Intermediate Similarity	NPD6101	Approved
0.701	Intermediate Similarity	NPD6904	Approved
0.701	Intermediate Similarity	NPD6080	Approved
0.701	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6616	Approved
0.6981	Remote Similarity	NPD6412	Phase 2
0.6979	Remote Similarity	NPD3573	Approved
0.6977	Remote Similarity	NPD3698	Phase 2
0.6964	Remote Similarity	NPD6313	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