NPASS Compound

Structure

CID58841 OpenBabel06191715392D 21 24 0 0 1 0 0 0 0 0999 V2000 2.5073 -0.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6722 -2.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8364 -2.4116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6700 -0.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6703 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1778 -1.4457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6714 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3425 -0.9634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8356 0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3431 -2.8933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5078 -2.4111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1781 -2.4106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8361 -1.4466 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0003 -0.9644 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6717 -0.9639 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8358 0.4822 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5075 -1.4461 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0443 -2.9102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 1.4822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 4 1 0 0 0 0 3 12 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 18 1 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 6 0 0 0 17 21 1 0 0 0 0 18 1 1 6 0 0 0 19 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.21
Volume:	315.262
LogP:	2.907
LogD:	2.694
LogS:	-3.165
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	4.081
Fsp3:	0.842
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.686
MDCK Permeability:	1.8527651263866574e-05
Pgp-inhibitor:	0.289
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.4

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.898
Plasma Protein Binding (PPB):	87.33647918701172%
Volume Distribution (VD):	0.852
Pgp-substrate:	5.0327582359313965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.375
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.78
CYP2C9-inhibitor:	0.162
CYP2C9-substrate:	0.268
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.794
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.351

ADMET: Excretion

Clearance (CL):	12.666
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.21
Drug-inuced Liver Injury (DILI):	0.378
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.888
Skin Sensitization:	0.385
Carcinogencity:	0.774
Eye Corrosion:	0.027
Eye Irritation:	0.049
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC58841

Natural Product ID:	NPC58841
*Common Name:**	(10R,13S,17S)-17-Hydroxy-10,13-Dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-Dodecahydrocyclopenta[A]Phenanthren-3-One
IUPAC Name:	(10R,13S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	MUMGGOZAMZWBJJ-PPORCNLBSA-N
Standard InCHI:	InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14?,15?,16?,17-,18-,19-/m0/s1
SMILES:	O=C1CC[C@]2(C(=C1)CCC1C2CC[C@]2(C1CC[C@@H]2O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL67934
PubChem CID:	5701998
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003568] Androstane steroids [CHEMONTID:0001467] Androgens and derivatives

*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
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23873	Penis cervi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31003	Moschus sifanicus	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2646	Moschus moschiferus	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23873	Penis cervi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO12246	Moschus chrysogaster	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO463	Moschus berezovskii	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO463	Moschus berezovskii	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31003	Moschus sifanicus	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2646	Moschus moschiferus	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2646	Moschus moschiferus	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO463	Moschus berezovskii	Species	Moschidae	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	4
Potency	4

Activity Type	# Activity
Individual Protein	4
ORGANISM	3
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[504033]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[504033]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[504033]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	268.5	nM	PMID[504033]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	19.94	%	PMID[504034]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	8.538	%	PMID[504035]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	0.0	%	PMID[504036]

☑ 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 NPC58841 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	158
0.1-0.2	1071
0.2-0.3	5521
0.3-0.4	15240
0.4-0.5	7060
0.5-0.6	6270
0.6-0.7	4757
0.7-0.8	2183
0.8-0.85	308
0.85-0.9	81
0.9-0.95	37
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC329043
1.0	High Similarity	NPC227064
1.0	High Similarity	NPC321187
1.0	High Similarity	NPC161423
0.9506	High Similarity	NPC327115
0.95	High Similarity	NPC214043
0.95	High Similarity	NPC82902
0.95	High Similarity	NPC85774
0.9398	High Similarity	NPC477943
0.9383	High Similarity	NPC474218
0.9268	High Similarity	NPC474733
0.9268	High Similarity	NPC145879
0.9268	High Similarity	NPC474732
0.9268	High Similarity	NPC474778
0.9268	High Similarity	NPC31564
0.9268	High Similarity	NPC469994
0.9259	High Similarity	NPC237712
0.9259	High Similarity	NPC473246
0.925	High Similarity	NPC193347
0.925	High Similarity	NPC151519
0.9167	High Similarity	NPC310010
0.9167	High Similarity	NPC326627
0.9157	High Similarity	NPC475740
0.9157	High Similarity	NPC58063
0.9157	High Similarity	NPC317590
0.9146	High Similarity	NPC469948
0.9146	High Similarity	NPC470574
0.9125	High Similarity	NPC6434
0.9048	High Similarity	NPC328539
0.9048	High Similarity	NPC328313
0.9036	High Similarity	NPC20688
0.9024	High Similarity	NPC59453
0.9024	High Similarity	NPC144258
0.9024	High Similarity	NPC221758
0.9	High Similarity	NPC2482
0.9	High Similarity	NPC472478
0.8966	High Similarity	NPC111015
0.8941	High Similarity	NPC76879
0.8941	High Similarity	NPC309603
0.8941	High Similarity	NPC26959
0.8941	High Similarity	NPC186688
0.8941	High Similarity	NPC473999
0.8941	High Similarity	NPC1015
0.8941	High Similarity	NPC268406
0.8941	High Similarity	NPC31985
0.8941	High Similarity	NPC2983
0.8929	High Similarity	NPC136548
0.8929	High Similarity	NPC93778
0.8916	High Similarity	NPC323765
0.8916	High Similarity	NPC471224
0.8889	High Similarity	NPC121984
0.8851	High Similarity	NPC233118
0.8851	High Similarity	NPC250575
0.8837	High Similarity	NPC320026
0.8837	High Similarity	NPC48010
0.8837	High Similarity	NPC171441
0.8824	High Similarity	NPC471722
0.881	High Similarity	NPC72133
0.881	High Similarity	NPC195640
0.881	High Similarity	NPC222613
0.881	High Similarity	NPC475022
0.881	High Similarity	NPC51014
0.881	High Similarity	NPC118648
0.8795	High Similarity	NPC472265
0.8736	High Similarity	NPC272746
0.8736	High Similarity	NPC168027
0.8736	High Similarity	NPC473998
0.8736	High Similarity	NPC475806
0.8736	High Similarity	NPC154101
0.8736	High Similarity	NPC185936
0.8721	High Similarity	NPC119416
0.8721	High Similarity	NPC275740
0.8721	High Similarity	NPC86319
0.8706	High Similarity	NPC472484
0.8706	High Similarity	NPC472481
0.8706	High Similarity	NPC90652
0.8706	High Similarity	NPC141292
0.8706	High Similarity	NPC472482
0.869	High Similarity	NPC474083
0.8667	High Similarity	NPC18509
0.8659	High Similarity	NPC136150
0.8652	High Similarity	NPC472932
0.8642	High Similarity	NPC472490
0.8636	High Similarity	NPC109305
0.8636	High Similarity	NPC474736
0.8636	High Similarity	NPC475255
0.8625	High Similarity	NPC197659
0.8621	High Similarity	NPC85173
0.8621	High Similarity	NPC69622
0.8621	High Similarity	NPC126993
0.8621	High Similarity	NPC191684
0.8605	High Similarity	NPC143767
0.8605	High Similarity	NPC292491
0.8605	High Similarity	NPC310752
0.8605	High Similarity	NPC470417
0.8605	High Similarity	NPC131470
0.8588	High Similarity	NPC155011
0.8588	High Similarity	NPC473168
0.8588	High Similarity	NPC94666
0.8571	High Similarity	NPC33913
0.8554	High Similarity	NPC320514
0.8539	High Similarity	NPC196485
0.8539	High Similarity	NPC8993
0.8539	High Similarity	NPC245972
0.8523	High Similarity	NPC131872
0.8523	High Similarity	NPC19114
0.8519	High Similarity	NPC82635
0.8506	High Similarity	NPC54689
0.8506	High Similarity	NPC32830
0.8506	High Similarity	NPC474245
0.85	High Similarity	NPC263582
0.85	High Similarity	NPC96319
0.8488	Intermediate Similarity	NPC96496
0.8488	Intermediate Similarity	NPC474684
0.8488	Intermediate Similarity	NPC142361
0.8478	Intermediate Similarity	NPC154072
0.8478	Intermediate Similarity	NPC144956
0.8471	Intermediate Similarity	NPC197823
0.8471	Intermediate Similarity	NPC29447
0.8471	Intermediate Similarity	NPC476426
0.8452	Intermediate Similarity	NPC476082
0.8452	Intermediate Similarity	NPC278648
0.8444	Intermediate Similarity	NPC271195
0.8444	Intermediate Similarity	NPC469599
0.8434	Intermediate Similarity	NPC14151
0.8434	Intermediate Similarity	NPC477372
0.8434	Intermediate Similarity	NPC116797
0.8434	Intermediate Similarity	NPC147066
0.8434	Intermediate Similarity	NPC3915
0.8427	Intermediate Similarity	NPC69454
0.8427	Intermediate Similarity	NPC66429
0.8427	Intermediate Similarity	NPC472930
0.8427	Intermediate Similarity	NPC152897
0.8427	Intermediate Similarity	NPC12722
0.8427	Intermediate Similarity	NPC470376
0.8427	Intermediate Similarity	NPC472942
0.8427	Intermediate Similarity	NPC470375
0.8427	Intermediate Similarity	NPC474807
0.8415	Intermediate Similarity	NPC308038
0.8415	Intermediate Similarity	NPC229204
0.8415	Intermediate Similarity	NPC474113
0.8415	Intermediate Similarity	NPC215843
0.8409	Intermediate Similarity	NPC129913
0.8409	Intermediate Similarity	NPC183283
0.8395	Intermediate Similarity	NPC106078
0.8395	Intermediate Similarity	NPC165711
0.8391	Intermediate Similarity	NPC471724
0.8391	Intermediate Similarity	NPC474677
0.8391	Intermediate Similarity	NPC53911
0.8391	Intermediate Similarity	NPC472483
0.8391	Intermediate Similarity	NPC193360
0.8391	Intermediate Similarity	NPC472802
0.8375	Intermediate Similarity	NPC114236
0.8372	Intermediate Similarity	NPC472985
0.8372	Intermediate Similarity	NPC158393
0.8372	Intermediate Similarity	NPC89077
0.8372	Intermediate Similarity	NPC194417
0.8372	Intermediate Similarity	NPC94755
0.8372	Intermediate Similarity	NPC472986
0.837	Intermediate Similarity	NPC235464
0.837	Intermediate Similarity	NPC197386
0.837	Intermediate Similarity	NPC147954
0.837	Intermediate Similarity	NPC166745
0.8353	Intermediate Similarity	NPC165064
0.8353	Intermediate Similarity	NPC25833
0.8353	Intermediate Similarity	NPC476412
0.8353	Intermediate Similarity	NPC472480
0.8353	Intermediate Similarity	NPC180834
0.8352	Intermediate Similarity	NPC49371
0.8352	Intermediate Similarity	NPC192428
0.8333	Intermediate Similarity	NPC103486
0.8333	Intermediate Similarity	NPC328351
0.8333	Intermediate Similarity	NPC46881
0.8333	Intermediate Similarity	NPC473172
0.8333	Intermediate Similarity	NPC212083
0.8333	Intermediate Similarity	NPC48362
0.8333	Intermediate Similarity	NPC310989
0.8315	Intermediate Similarity	NPC155304
0.8315	Intermediate Similarity	NPC63748
0.8315	Intermediate Similarity	NPC233116
0.8315	Intermediate Similarity	NPC262870
0.8313	Intermediate Similarity	NPC172013
0.8313	Intermediate Similarity	NPC476809
0.8313	Intermediate Similarity	NPC45495
0.8298	Intermediate Similarity	NPC87351
0.8298	Intermediate Similarity	NPC477915
0.8295	Intermediate Similarity	NPC476733
0.8295	Intermediate Similarity	NPC475921
0.8295	Intermediate Similarity	NPC472971
0.8295	Intermediate Similarity	NPC215029
0.8295	Intermediate Similarity	NPC474704
0.8295	Intermediate Similarity	NPC472970
0.8295	Intermediate Similarity	NPC472477
0.8295	Intermediate Similarity	NPC472475
0.8293	Intermediate Similarity	NPC62336
0.8293	Intermediate Similarity	NPC477522
0.8293	Intermediate Similarity	NPC477514
0.828	Intermediate Similarity	NPC474720
0.8276	Intermediate Similarity	NPC233836
0.8276	Intermediate Similarity	NPC187376

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 NPC58841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1391
0.2-0.3	4119
0.3-0.4	2455
0.4-0.5	560
0.5-0.6	159
0.6-0.7	114
0.7-0.8	127
0.8-0.85	45
0.85-0.9	26
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3133	Approved
1.0	High Similarity	NPD3665	Phase 1
1.0	High Similarity	NPD3666	Approved
0.9268	High Similarity	NPD3618	Phase 1
0.925	High Similarity	NPD4221	Approved
0.925	High Similarity	NPD4223	Phase 3
0.925	High Similarity	NPD3667	Approved
0.9167	High Similarity	NPD4753	Phase 2
0.907	High Similarity	NPD4202	Approved
0.9024	High Similarity	NPD4786	Approved
0.9024	High Similarity	NPD4197	Approved
0.8941	High Similarity	NPD5328	Approved
0.8916	High Similarity	NPD5329	Approved
0.881	High Similarity	NPD5205	Approved
0.881	High Similarity	NPD4689	Approved
0.881	High Similarity	NPD5330	Approved
0.881	High Similarity	NPD7521	Approved
0.881	High Similarity	NPD4688	Approved
0.881	High Similarity	NPD6409	Approved
0.881	High Similarity	NPD7334	Approved
0.881	High Similarity	NPD4690	Approved
0.881	High Similarity	NPD4138	Approved
0.881	High Similarity	NPD4693	Phase 3
0.881	High Similarity	NPD6684	Approved
0.881	High Similarity	NPD5279	Phase 3
0.881	High Similarity	NPD7146	Approved
0.8736	High Similarity	NPD6079	Approved
0.8667	High Similarity	NPD4755	Approved
0.8652	High Similarity	NPD4629	Approved
0.8652	High Similarity	NPD5210	Approved
0.8605	High Similarity	NPD7513	Clinical (unspecified phase)
0.8605	High Similarity	NPD6903	Approved
0.8588	High Similarity	NPD5690	Phase 2
0.8588	High Similarity	NPD5280	Approved
0.8588	High Similarity	NPD4694	Approved
0.8519	High Similarity	NPD3617	Approved
0.85	High Similarity	NPD3701	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD4696	Approved
0.8478	Intermediate Similarity	NPD5286	Approved
0.8478	Intermediate Similarity	NPD5285	Approved
0.8478	Intermediate Similarity	NPD4700	Approved
0.8462	Intermediate Similarity	NPD6083	Phase 2
0.8462	Intermediate Similarity	NPD6084	Phase 2
0.8452	Intermediate Similarity	NPD4788	Approved
0.8415	Intermediate Similarity	NPD4195	Approved
0.8387	Intermediate Similarity	NPD5223	Approved
0.8372	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD3668	Phase 3
0.8352	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD5222	Approved
0.8352	Intermediate Similarity	NPD5221	Approved
0.8352	Intermediate Similarity	NPD4697	Phase 3
0.8298	Intermediate Similarity	NPD5211	Phase 2
0.8298	Intermediate Similarity	NPD5226	Approved
0.8298	Intermediate Similarity	NPD4633	Approved
0.8298	Intermediate Similarity	NPD5224	Approved
0.8298	Intermediate Similarity	NPD5225	Approved
0.8261	Intermediate Similarity	NPD5173	Approved
0.8242	Intermediate Similarity	NPD5695	Phase 3
0.8211	Intermediate Similarity	NPD5174	Approved
0.8211	Intermediate Similarity	NPD5175	Approved
0.8211	Intermediate Similarity	NPD4754	Approved
0.8205	Intermediate Similarity	NPD4137	Phase 3
0.8172	Intermediate Similarity	NPD5696	Approved
0.8125	Intermediate Similarity	NPD5141	Approved
0.8111	Intermediate Similarity	NPD5284	Approved
0.8111	Intermediate Similarity	NPD7515	Phase 2
0.8111	Intermediate Similarity	NPD5281	Approved
0.8101	Intermediate Similarity	NPD4691	Approved
0.8101	Intermediate Similarity	NPD4747	Approved
0.8095	Intermediate Similarity	NPD4695	Discontinued
0.8041	Intermediate Similarity	NPD7128	Approved
0.8041	Intermediate Similarity	NPD4767	Approved
0.8041	Intermediate Similarity	NPD6675	Approved
0.8041	Intermediate Similarity	NPD4768	Approved
0.8041	Intermediate Similarity	NPD6402	Approved
0.8041	Intermediate Similarity	NPD5739	Approved
0.8022	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD4096	Approved
0.8	Intermediate Similarity	NPD4139	Approved
0.8	Intermediate Similarity	NPD4692	Approved
0.7978	Intermediate Similarity	NPD5737	Approved
0.7978	Intermediate Similarity	NPD5208	Approved
0.7978	Intermediate Similarity	NPD6672	Approved
0.7975	Intermediate Similarity	NPD3698	Phase 2
0.7959	Intermediate Similarity	NPD6412	Phase 2
0.7959	Intermediate Similarity	NPD5701	Approved
0.7959	Intermediate Similarity	NPD5697	Approved
0.7955	Intermediate Similarity	NPD4623	Approved
0.7955	Intermediate Similarity	NPD4519	Discontinued
0.7927	Intermediate Similarity	NPD6942	Approved
0.7927	Intermediate Similarity	NPD7339	Approved
0.7889	Intermediate Similarity	NPD6080	Approved
0.7889	Intermediate Similarity	NPD6904	Approved
0.7889	Intermediate Similarity	NPD6673	Approved
0.7879	Intermediate Similarity	NPD6881	Approved
0.7879	Intermediate Similarity	NPD4729	Approved
0.7879	Intermediate Similarity	NPD6899	Approved
0.7879	Intermediate Similarity	NPD4730	Approved
0.7879	Intermediate Similarity	NPD5128	Approved
0.7879	Intermediate Similarity	NPD7320	Approved
0.7879	Intermediate Similarity	NPD6011	Approved
0.7875	Intermediate Similarity	NPD4244	Approved
0.7875	Intermediate Similarity	NPD4245	Approved
0.7826	Intermediate Similarity	NPD5133	Approved
0.7805	Intermediate Similarity	NPD4058	Approved
0.78	Intermediate Similarity	NPD6013	Approved
0.78	Intermediate Similarity	NPD6373	Approved
0.78	Intermediate Similarity	NPD6372	Approved
0.78	Intermediate Similarity	NPD6012	Approved
0.78	Intermediate Similarity	NPD6014	Approved
0.7778	Intermediate Similarity	NPD4243	Approved
0.7778	Intermediate Similarity	NPD4518	Approved
0.7753	Intermediate Similarity	NPD6098	Approved
0.7742	Intermediate Similarity	NPD7748	Approved
0.7723	Intermediate Similarity	NPD7290	Approved
0.7723	Intermediate Similarity	NPD5135	Approved
0.7723	Intermediate Similarity	NPD6883	Approved
0.7723	Intermediate Similarity	NPD5169	Approved
0.7723	Intermediate Similarity	NPD5248	Approved
0.7723	Intermediate Similarity	NPD4634	Approved
0.7723	Intermediate Similarity	NPD5250	Approved
0.7723	Intermediate Similarity	NPD5251	Approved
0.7723	Intermediate Similarity	NPD5249	Phase 3
0.7723	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7102	Approved
0.7723	Intermediate Similarity	NPD5247	Approved
0.7717	Intermediate Similarity	NPD5693	Phase 1
0.766	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6650	Approved
0.7647	Intermediate Similarity	NPD5127	Approved
0.7647	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5216	Approved
0.7647	Intermediate Similarity	NPD8130	Phase 1
0.7647	Intermediate Similarity	NPD5215	Approved
0.7647	Intermediate Similarity	NPD5217	Approved
0.7647	Intermediate Similarity	NPD6617	Approved
0.7647	Intermediate Similarity	NPD6869	Approved
0.7647	Intermediate Similarity	NPD6847	Approved
0.7647	Intermediate Similarity	NPD6649	Approved
0.764	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5207	Approved
0.7609	Intermediate Similarity	NPD5692	Phase 3
0.7604	Intermediate Similarity	NPD7638	Approved
0.759	Intermediate Similarity	NPD4687	Approved
0.759	Intermediate Similarity	NPD5733	Approved
0.759	Intermediate Similarity	NPD4784	Approved
0.759	Intermediate Similarity	NPD4785	Approved
0.7573	Intermediate Similarity	NPD6882	Approved
0.7573	Intermediate Similarity	NPD8297	Approved
0.7561	Intermediate Similarity	NPD5276	Approved
0.7553	Intermediate Similarity	NPD6001	Approved
0.7551	Intermediate Similarity	NPD5091	Approved
0.7531	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6050	Approved
0.7527	Intermediate Similarity	NPD5694	Approved
0.7526	Intermediate Similarity	NPD7640	Approved
0.7526	Intermediate Similarity	NPD7639	Approved
0.7525	Intermediate Similarity	NPD5168	Approved
0.75	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD5275	Approved
0.75	Intermediate Similarity	NPD4190	Phase 3
0.7473	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7525	Registered
0.7468	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5167	Approved
0.7381	Intermediate Similarity	NPD6924	Approved
0.7381	Intermediate Similarity	NPD6926	Approved
0.7358	Intermediate Similarity	NPD6274	Approved
0.7349	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6008	Approved
0.7312	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6009	Approved
0.729	Intermediate Similarity	NPD6317	Approved
0.7273	Intermediate Similarity	NPD4748	Discontinued
0.7245	Intermediate Similarity	NPD5290	Discontinued
0.7229	Intermediate Similarity	NPD4789	Approved
0.7222	Intermediate Similarity	NPD6335	Approved
0.7222	Intermediate Similarity	NPD6313	Approved
0.7222	Intermediate Similarity	NPD6314	Approved
0.7209	Intermediate Similarity	NPD6933	Approved
0.7188	Intermediate Similarity	NPD7900	Approved
0.7188	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7645	Phase 2
0.7156	Intermediate Similarity	NPD7101	Approved
0.7156	Intermediate Similarity	NPD7100	Approved
0.7156	Intermediate Similarity	NPD4522	Approved
0.7113	Intermediate Similarity	NPD5654	Approved
0.7111	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6922	Approved
0.7108	Intermediate Similarity	NPD6923	Approved
0.7097	Intermediate Similarity	NPD3573	Approved
0.7093	Intermediate Similarity	NPD3703	Phase 2
0.7091	Intermediate Similarity	NPD6054	Approved
0.7091	Intermediate Similarity	NPD6319	Approved
0.7091	Intermediate Similarity	NPD6059	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