NPASS Compound

Structure

NPC470960 OpenBabel07101718192D 33 39 0 0 1 0 0 0 0 0999 V2000 9.0130 -0.5737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9179 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8592 1.0698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 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 3.6720 1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6665 2.0827 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 -0.0000 -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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3386 -0.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7206 1.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0768 -0.2223 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 6.0514 0.9612 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0733 1.1691 0.0000 C 0 0 2 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 6.3604 0.0102 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5197 -0.7550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0077 0.5454 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8287 -1.7061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6987 1.4965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7558 -0.6516 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 4 27 1 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 11 25 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 14 31 1 0 0 0 0 15 24 1 0 0 0 0 15 26 1 0 0 0 0 16 12 1 1 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 14 1 6 0 0 0 17 19 1 0 0 0 0 17 21 1 0 0 0 0 18 25 1 6 0 0 0 19 25 1 6 0 0 0 20 27 1 6 0 0 0 21 13 1 6 0 0 0 21 32 1 0 0 0 0 22 27 1 0 0 0 0 22 29 2 0 0 0 0 23 28 1 6 0 0 0 23 33 1 0 0 0 0 24 30 2 0 0 0 0 24 32 1 0 0 0 0 25 2 1 6 0 0 0 26 3 1 1 0 0 0 26 31 1 0 0 0 0 27 28 1 6 0 0 0 28 10 1 1 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.25
Volume:	486.984
LogP:	2.959
LogD:	2.156
LogS:	-4.211
# Rotatable Bonds:	3
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	5.407
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.845
MDCK Permeability:	2.2622214601142332e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.743
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.958
Plasma Protein Binding (PPB):	81.69639587402344%
Volume Distribution (VD):	0.876
Pgp-substrate:	13.214302062988281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.704
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.887
CYP3A4-substrate:	0.919

ADMET: Excretion

Clearance (CL):	4.933
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.155
Human Hepatotoxicity (H-HT):	0.594
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.655
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.89
Carcinogencity:	0.899
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC470960

Natural Product ID:	NPC470960
*Common Name:**	Withametelin F
IUPAC Name:	n.a.
Synonyms:	Withametelin F
Standard InCHIKey:	TWSTVCZSHMUIOQ-ZPRSOMTPSA-N
Standard InCHI:	InChI=1S/C28H36O5/c1-15-24(30)32-21-13-26(15,3)31-14-17(21)19-8-7-18-16-12-23-28(33-23)10-5-6-22(29)27(28,4)20(16)9-11-25(18,19)2/h5-6,16-21,23H,1,7-14H2,2-4H3/t16-,17-,18-,19+,20-,21+,23+,25-,26-,27-,28+/m0/s1
SMILES:	O=C1O[C@@H]2C[C@](C1=C)(C)OC[C@H]2[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]2[C@]3([C@]1(C)C(=O)C=CC3)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2333592
PubChem CID:	71718234
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO22157	Datura wrightii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23252848]
NPO22157	Datura wrightii	Species	Solanaceae	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	4
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	Ratio IC50	=	6.0	n.a.	PMID[495203]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	3300.0	nM	PMID[495203]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	1400.0	nM	PMID[495203]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1500.0	nM	PMID[495203]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	560.0	nM	PMID[495203]

☑ 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 NPC470960 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	287
0.1-0.2	1718
0.2-0.3	5102
0.3-0.4	9605
0.4-0.5	11893
0.5-0.6	6368
0.6-0.7	5703
0.7-0.8	1912
0.8-0.85	91
0.85-0.9	14
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9358	High Similarity	NPC476960
0.9174	High Similarity	NPC470959
0.9174	High Similarity	NPC476965
0.9126	High Similarity	NPC470954
0.8929	High Similarity	NPC476961
0.8919	High Similarity	NPC473720
0.8899	High Similarity	NPC122056
0.886	High Similarity	NPC204812
0.8839	High Similarity	NPC475520
0.8818	High Similarity	NPC470953
0.8783	High Similarity	NPC241456
0.8783	High Similarity	NPC32868
0.8761	High Similarity	NPC476962
0.8739	High Similarity	NPC270929
0.8692	High Similarity	NPC476958
0.8661	High Similarity	NPC286528
0.8661	High Similarity	NPC140055
0.8661	High Similarity	NPC20302
0.8661	High Similarity	NPC167606
0.8609	High Similarity	NPC170538
0.8584	High Similarity	NPC329736
0.8584	High Similarity	NPC50774
0.8584	High Similarity	NPC709
0.8571	High Similarity	NPC476963
0.8534	High Similarity	NPC11895
0.8534	High Similarity	NPC469789
0.8509	High Similarity	NPC61520
0.8509	High Similarity	NPC264954
0.8505	High Similarity	NPC189616
0.8496	Intermediate Similarity	NPC183580
0.8496	Intermediate Similarity	NPC312824
0.8496	Intermediate Similarity	NPC243065
0.8496	Intermediate Similarity	NPC470492
0.8496	Intermediate Similarity	NPC470493
0.8482	Intermediate Similarity	NPC67259
0.8482	Intermediate Similarity	NPC147912
0.8475	Intermediate Similarity	NPC287423
0.8462	Intermediate Similarity	NPC8369
0.8435	Intermediate Similarity	NPC474370
0.8396	Intermediate Similarity	NPC310981
0.839	Intermediate Similarity	NPC293112
0.839	Intermediate Similarity	NPC473635
0.8381	Intermediate Similarity	NPC176845
0.8381	Intermediate Similarity	NPC252295
0.8378	Intermediate Similarity	NPC474315
0.8362	Intermediate Similarity	NPC67569
0.8349	Intermediate Similarity	NPC470952
0.8348	Intermediate Similarity	NPC470495
0.8333	Intermediate Similarity	NPC218301
0.8333	Intermediate Similarity	NPC476959
0.8305	Intermediate Similarity	NPC81736
0.8305	Intermediate Similarity	NPC172154
0.8304	Intermediate Similarity	NPC476964
0.8304	Intermediate Similarity	NPC476163
0.8291	Intermediate Similarity	NPC153700
0.8291	Intermediate Similarity	NPC470265
0.8291	Intermediate Similarity	NPC23786
0.8291	Intermediate Similarity	NPC88326
0.8286	Intermediate Similarity	NPC38530
0.8286	Intermediate Similarity	NPC292133
0.8286	Intermediate Similarity	NPC84335
0.8286	Intermediate Similarity	NPC2049
0.8261	Intermediate Similarity	NPC113448
0.8261	Intermediate Similarity	NPC470420
0.8252	Intermediate Similarity	NPC79117
0.825	Intermediate Similarity	NPC473620
0.822	Intermediate Similarity	NPC120724
0.819	Intermediate Similarity	NPC58052
0.819	Intermediate Similarity	NPC473274
0.819	Intermediate Similarity	NPC111684
0.819	Intermediate Similarity	NPC307164
0.819	Intermediate Similarity	NPC473203
0.8182	Intermediate Similarity	NPC91034
0.8182	Intermediate Similarity	NPC475294
0.8174	Intermediate Similarity	NPC239273
0.8173	Intermediate Similarity	NPC470697
0.8158	Intermediate Similarity	NPC284915
0.8158	Intermediate Similarity	NPC238667
0.8151	Intermediate Similarity	NPC8374
0.8151	Intermediate Similarity	NPC3381
0.8151	Intermediate Similarity	NPC470494
0.8142	Intermediate Similarity	NPC475524
0.8142	Intermediate Similarity	NPC100267
0.8131	Intermediate Similarity	NPC475392
0.8131	Intermediate Similarity	NPC470906
0.8131	Intermediate Similarity	NPC475202
0.8131	Intermediate Similarity	NPC475385
0.813	Intermediate Similarity	NPC316915
0.8125	Intermediate Similarity	NPC253906
0.8113	Intermediate Similarity	NPC151488
0.8113	Intermediate Similarity	NPC473456
0.8113	Intermediate Similarity	NPC110937
0.8113	Intermediate Similarity	NPC226986
0.8113	Intermediate Similarity	NPC23680
0.8108	Intermediate Similarity	NPC177064
0.8103	Intermediate Similarity	NPC311554
0.8103	Intermediate Similarity	NPC186525
0.8103	Intermediate Similarity	NPC257457
0.8095	Intermediate Similarity	NPC33473
0.8091	Intermediate Similarity	NPC60681
0.8073	Intermediate Similarity	NPC473283
0.8073	Intermediate Similarity	NPC329345
0.8073	Intermediate Similarity	NPC36321
0.8073	Intermediate Similarity	NPC475526
0.8073	Intermediate Similarity	NPC254202
0.8058	Intermediate Similarity	NPC152467
0.8058	Intermediate Similarity	NPC161638
0.8051	Intermediate Similarity	NPC470878
0.8051	Intermediate Similarity	NPC473256
0.8049	Intermediate Similarity	NPC231240
0.8036	Intermediate Similarity	NPC474242
0.8036	Intermediate Similarity	NPC474901
0.8036	Intermediate Similarity	NPC475941
0.8036	Intermediate Similarity	NPC41405
0.8019	Intermediate Similarity	NPC106425
0.8019	Intermediate Similarity	NPC122324
0.8019	Intermediate Similarity	NPC151725
0.8018	Intermediate Similarity	NPC220974
0.8017	Intermediate Similarity	NPC473253
0.8017	Intermediate Similarity	NPC474518
0.8	Intermediate Similarity	NPC38830
0.8	Intermediate Similarity	NPC473435
0.8	Intermediate Similarity	NPC471078
0.8	Intermediate Similarity	NPC473431
0.8	Intermediate Similarity	NPC473280
0.7982	Intermediate Similarity	NPC69291
0.7982	Intermediate Similarity	NPC277769
0.7982	Intermediate Similarity	NPC185530
0.7982	Intermediate Similarity	NPC40918
0.7982	Intermediate Similarity	NPC475970
0.7982	Intermediate Similarity	NPC136289
0.7982	Intermediate Similarity	NPC320447
0.7981	Intermediate Similarity	NPC49420
0.7965	Intermediate Similarity	NPC37116
0.7965	Intermediate Similarity	NPC473627
0.7963	Intermediate Similarity	NPC112167
0.7963	Intermediate Similarity	NPC476303
0.7961	Intermediate Similarity	NPC177141
0.7961	Intermediate Similarity	NPC73995
0.7946	Intermediate Similarity	NPC475418
0.7946	Intermediate Similarity	NPC473482
0.7946	Intermediate Similarity	NPC473483
0.7946	Intermediate Similarity	NPC318363
0.7941	Intermediate Similarity	NPC30421
0.7931	Intermediate Similarity	NPC148458
0.7931	Intermediate Similarity	NPC64318
0.7928	Intermediate Similarity	NPC470975
0.7928	Intermediate Similarity	NPC103088
0.7928	Intermediate Similarity	NPC470979
0.7925	Intermediate Similarity	NPC476519
0.7925	Intermediate Similarity	NPC274417
0.7913	Intermediate Similarity	NPC25909
0.7909	Intermediate Similarity	NPC72151
0.7909	Intermediate Similarity	NPC180204
0.7909	Intermediate Similarity	NPC476889
0.7909	Intermediate Similarity	NPC176883
0.7909	Intermediate Similarity	NPC26478
0.7909	Intermediate Similarity	NPC112009
0.7899	Intermediate Similarity	NPC310511
0.7899	Intermediate Similarity	NPC46570
0.7899	Intermediate Similarity	NPC204731
0.7895	Intermediate Similarity	NPC474229
0.789	Intermediate Similarity	NPC168319
0.789	Intermediate Similarity	NPC474327
0.789	Intermediate Similarity	NPC473514
0.789	Intermediate Similarity	NPC93744
0.789	Intermediate Similarity	NPC81530
0.789	Intermediate Similarity	NPC476223
0.789	Intermediate Similarity	NPC224720
0.789	Intermediate Similarity	NPC194028
0.789	Intermediate Similarity	NPC476888
0.789	Intermediate Similarity	NPC476240
0.7886	Intermediate Similarity	NPC470880
0.7886	Intermediate Similarity	NPC473593
0.7886	Intermediate Similarity	NPC476966
0.7886	Intermediate Similarity	NPC231529
0.7885	Intermediate Similarity	NPC273199
0.7885	Intermediate Similarity	NPC475965
0.7885	Intermediate Similarity	NPC474842
0.7881	Intermediate Similarity	NPC473270
0.7881	Intermediate Similarity	NPC42673
0.7876	Intermediate Similarity	NPC475065
0.7876	Intermediate Similarity	NPC469370
0.787	Intermediate Similarity	NPC98868
0.787	Intermediate Similarity	NPC471582
0.787	Intermediate Similarity	NPC114274
0.7869	Intermediate Similarity	NPC42399
0.7864	Intermediate Similarity	NPC215831
0.7863	Intermediate Similarity	NPC471854
0.7857	Intermediate Similarity	NPC330011
0.7857	Intermediate Similarity	NPC44063
0.7857	Intermediate Similarity	NPC475570
0.7857	Intermediate Similarity	NPC329048
0.7857	Intermediate Similarity	NPC263729
0.785	Intermediate Similarity	NPC471775
0.7838	Intermediate Similarity	NPC470297
0.7838	Intermediate Similarity	NPC137657
0.7833	Intermediate Similarity	NPC107493
0.7833	Intermediate Similarity	NPC269642
0.783	Intermediate Similarity	NPC269729

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 NPC470960 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	1766
0.2-0.3	3896
0.3-0.4	2152
0.4-0.5	662
0.5-0.6	192
0.6-0.7	159
0.7-0.8	80
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8661	High Similarity	NPD7115	Discovery
0.8091	Intermediate Similarity	NPD6008	Approved
0.7946	Intermediate Similarity	NPD6899	Approved
0.7946	Intermediate Similarity	NPD6881	Approved
0.7941	Intermediate Similarity	NPD3573	Approved
0.7895	Intermediate Similarity	NPD6650	Approved
0.7895	Intermediate Similarity	NPD6649	Approved
0.7857	Intermediate Similarity	NPD5697	Approved
0.7807	Intermediate Similarity	NPD6883	Approved
0.7807	Intermediate Similarity	NPD7290	Approved
0.7807	Intermediate Similarity	NPD7102	Approved
0.7768	Intermediate Similarity	NPD5739	Approved
0.7768	Intermediate Similarity	NPD6675	Approved
0.7768	Intermediate Similarity	NPD6402	Approved
0.7768	Intermediate Similarity	NPD7128	Approved
0.7757	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD6847	Approved
0.7739	Intermediate Similarity	NPD8130	Phase 1
0.7739	Intermediate Similarity	NPD6617	Approved
0.7739	Intermediate Similarity	NPD6869	Approved
0.7719	Intermediate Similarity	NPD6012	Approved
0.7719	Intermediate Similarity	NPD6014	Approved
0.7719	Intermediate Similarity	NPD6372	Approved
0.7719	Intermediate Similarity	NPD6013	Approved
0.7719	Intermediate Similarity	NPD6373	Approved
0.7672	Intermediate Similarity	NPD6882	Approved
0.7672	Intermediate Similarity	NPD8297	Approved
0.7664	Intermediate Similarity	NPD7900	Approved
0.7664	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6079	Approved
0.7632	Intermediate Similarity	NPD6011	Approved
0.7632	Intermediate Similarity	NPD7320	Approved
0.757	Intermediate Similarity	NPD6399	Phase 3
0.7544	Intermediate Similarity	NPD5701	Approved
0.7524	Intermediate Similarity	NPD6672	Approved
0.7524	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD7748	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7477	Intermediate Similarity	NPD5693	Phase 1
0.7477	Intermediate Similarity	NPD5285	Approved
0.7477	Intermediate Similarity	NPD5286	Approved
0.7477	Intermediate Similarity	NPD4696	Approved
0.7455	Intermediate Similarity	NPD7902	Approved
0.7453	Intermediate Similarity	NPD5328	Approved
0.7404	Intermediate Similarity	NPD1694	Approved
0.7377	Intermediate Similarity	NPD6319	Approved
0.7368	Intermediate Similarity	NPD5141	Approved
0.7364	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD5221	Approved
0.7364	Intermediate Similarity	NPD5222	Approved
0.7358	Intermediate Similarity	NPD6903	Approved
0.7345	Intermediate Similarity	NPD4633	Approved
0.7345	Intermediate Similarity	NPD5226	Approved
0.7345	Intermediate Similarity	NPD5224	Approved
0.7345	Intermediate Similarity	NPD5225	Approved
0.7339	Intermediate Similarity	NPD6001	Approved
0.7315	Intermediate Similarity	NPD7515	Phase 2
0.7297	Intermediate Similarity	NPD6083	Phase 2
0.7297	Intermediate Similarity	NPD6084	Phase 2
0.7297	Intermediate Similarity	NPD4755	Approved
0.7297	Intermediate Similarity	NPD5173	Approved
0.7295	Intermediate Similarity	NPD7100	Approved
0.7295	Intermediate Similarity	NPD7101	Approved
0.729	Intermediate Similarity	NPD6904	Approved
0.729	Intermediate Similarity	NPD6080	Approved
0.729	Intermediate Similarity	NPD6673	Approved
0.7288	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5175	Approved
0.7281	Intermediate Similarity	NPD5174	Approved
0.728	Intermediate Similarity	NPD7492	Approved
0.7257	Intermediate Similarity	NPD5223	Approved
0.7244	Intermediate Similarity	NPD7736	Approved
0.7236	Intermediate Similarity	NPD6054	Approved
0.7232	Intermediate Similarity	NPD5696	Approved
0.7232	Intermediate Similarity	NPD4225	Approved
0.7232	Intermediate Similarity	NPD7638	Approved
0.7222	Intermediate Similarity	NPD6616	Approved
0.7213	Intermediate Similarity	NPD6335	Approved
0.7207	Intermediate Similarity	NPD4697	Phase 3
0.7203	Intermediate Similarity	NPD4634	Approved
0.719	Intermediate Similarity	NPD6868	Approved
0.719	Intermediate Similarity	NPD6274	Approved
0.7188	Intermediate Similarity	NPD7319	Approved
0.717	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3618	Phase 1
0.7168	Intermediate Similarity	NPD4700	Approved
0.7168	Intermediate Similarity	NPD7640	Approved
0.7168	Intermediate Similarity	NPD7639	Approved
0.7167	Intermediate Similarity	NPD4632	Approved
0.7165	Intermediate Similarity	NPD7078	Approved
0.7156	Intermediate Similarity	NPD6411	Approved
0.7131	Intermediate Similarity	NPD6317	Approved
0.712	Intermediate Similarity	NPD6370	Approved
0.7117	Intermediate Similarity	NPD5695	Phase 3
0.7115	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7507	Approved
0.7073	Intermediate Similarity	NPD6314	Approved
0.7073	Intermediate Similarity	NPD6313	Approved
0.7064	Intermediate Similarity	NPD5207	Approved
0.7063	Intermediate Similarity	NPD8328	Phase 3
0.7063	Intermediate Similarity	NPD7604	Phase 2
0.704	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6015	Approved
0.704	Intermediate Similarity	NPD6016	Approved
0.7037	Intermediate Similarity	NPD5208	Approved
0.7034	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4729	Approved
0.7034	Intermediate Similarity	NPD4730	Approved
0.7009	Intermediate Similarity	NPD6098	Approved
0.7	Intermediate Similarity	NPD8035	Phase 2
0.7	Intermediate Similarity	NPD8034	Phase 2
0.7	Intermediate Similarity	NPD5694	Approved
0.7	Intermediate Similarity	NPD6050	Approved
0.6992	Remote Similarity	NPD6009	Approved
0.6984	Remote Similarity	NPD5988	Approved
0.6981	Remote Similarity	NPD4786	Approved
0.6972	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6051	Approved
0.6972	Remote Similarity	NPD6101	Approved
0.6964	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4629	Approved
0.6964	Remote Similarity	NPD5210	Approved
0.696	Remote Similarity	NPD6059	Approved
0.6937	Remote Similarity	NPD4202	Approved
0.6917	Remote Similarity	NPD5247	Approved
0.6917	Remote Similarity	NPD5251	Approved
0.6917	Remote Similarity	NPD5248	Approved
0.6917	Remote Similarity	NPD5249	Phase 3
0.6917	Remote Similarity	NPD5250	Approved
0.6917	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5785	Approved
0.6909	Remote Similarity	NPD5692	Phase 3
0.6905	Remote Similarity	NPD6908	Approved
0.6905	Remote Similarity	NPD6909	Approved
0.6905	Remote Similarity	NPD5983	Phase 2
0.6899	Remote Similarity	NPD8293	Discontinued
0.6891	Remote Similarity	NPD5128	Approved
0.6864	Remote Similarity	NPD4767	Approved
0.6864	Remote Similarity	NPD4768	Approved
0.686	Remote Similarity	NPD5217	Approved
0.686	Remote Similarity	NPD5215	Approved
0.686	Remote Similarity	NPD5216	Approved
0.6847	Remote Similarity	NPD5284	Approved
0.6847	Remote Similarity	NPD5281	Approved
0.6838	Remote Similarity	NPD4754	Approved
0.6833	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6336	Discontinued
0.6822	Remote Similarity	NPD3668	Phase 3
0.6818	Remote Similarity	NPD4753	Phase 2
0.6807	Remote Similarity	NPD6614	Approved
0.6803	Remote Similarity	NPD6053	Discontinued
0.6792	Remote Similarity	NPD3667	Approved
0.6777	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5135	Approved
0.6777	Remote Similarity	NPD5169	Approved
0.6772	Remote Similarity	NPD8033	Approved
0.6772	Remote Similarity	NPD8513	Phase 3
0.6772	Remote Similarity	NPD7503	Approved
0.6772	Remote Similarity	NPD8516	Approved
0.6772	Remote Similarity	NPD8517	Approved
0.6772	Remote Similarity	NPD8515	Approved
0.6759	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5168	Approved
0.6721	Remote Similarity	NPD5127	Approved
0.672	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6052	Approved
0.6693	Remote Similarity	NPD8377	Approved
0.6693	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD3665	Phase 1
0.6641	Remote Similarity	NPD8378	Approved
0.6641	Remote Similarity	NPD8335	Approved
0.6641	Remote Similarity	NPD8379	Approved
0.6641	Remote Similarity	NPD8380	Approved
0.6641	Remote Similarity	NPD8296	Approved
0.6637	Remote Similarity	NPD5779	Approved
0.6637	Remote Similarity	NPD5778	Approved
0.6636	Remote Similarity	NPD4221	Approved
0.6636	Remote Similarity	NPD4223	Phase 3
0.6613	Remote Similarity	NPD8133	Approved
0.6612	Remote Similarity	NPD6686	Approved
0.661	Remote Similarity	NPD7632	Discontinued
0.6609	Remote Similarity	NPD7732	Phase 3
0.6606	Remote Similarity	NPD5329	Approved
0.6567	Remote Similarity	NPD7260	Phase 2
0.656	Remote Similarity	NPD5167	Approved
0.6552	Remote Similarity	NPD5959	Approved
0.6549	Remote Similarity	NPD7637	Suspended
0.6545	Remote Similarity	NPD5690	Phase 2
0.6535	Remote Similarity	NPD7328	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