NPASS Compound

Structure

CID230513 OpenBabel06191716022D 35 40 0 0 1 0 0 0 0 0999 V2000 -6.6611 -1.9179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8280 1.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2315 0.4436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7336 -1.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1630 2.4051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3304 2.8855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4985 -0.4799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3313 0.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8286 -0.4769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8326 1.4430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0011 -1.9226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9972 -2.8791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8289 -1.4377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9961 0.9641 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6656 0.9623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9969 -1.9183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1639 1.4443 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4985 1.4435 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6659 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9964 0.0033 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8320 -1.4420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8336 -1.4420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 0.9618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8325 -0.4807 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1647 -1.4382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3310 0.9631 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8331 -0.4807 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 -5.8294 -3.3593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7101 -1.9477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7090 0.0251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3327 -1.9188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0119 -0.0003 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2778 -0.4802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1644 -0.4773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 26 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 29 1 0 0 0 0 13 16 2 0 0 0 0 14 2 1 1 0 0 0 14 17 1 0 0 0 0 15 10 1 6 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 25 1 0 0 0 0 17 26 1 1 0 0 0 18 26 1 1 0 0 0 19 27 1 1 0 0 0 20 14 1 6 0 0 0 20 35 1 0 0 0 0 21 11 1 1 0 0 0 21 24 1 0 0 0 0 21 34 1 0 0 0 0 22 27 1 0 0 0 0 22 30 2 0 0 0 0 23 28 1 1 0 0 0 23 34 1 0 0 0 0 24 28 1 1 0 0 0 24 31 1 0 0 0 0 25 32 2 0 0 0 0 25 35 1 0 0 0 0 26 3 1 1 0 0 0 27 28 1 1 0 0 0 28 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.28
Volume:	495.128
LogP:	3.17
LogD:	3.156
LogS:	-4.349
# Rotatable Bonds:	3
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	6.152
Fsp3:	0.857
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:	-5.119
MDCK Permeability:	1.6856949514476582e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.185
30% Bioavailability (F30%):	0.516

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.427
Plasma Protein Binding (PPB):	71.90863800048828%
Volume Distribution (VD):	0.966
Pgp-substrate:	13.371554374694824%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.758
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.781
CYP3A4-substrate:	0.569

ADMET: Excretion

Clearance (CL):	7.63
Half-life (T1/2):	0.837

ADMET: Toxicity

hERG Blockers:	0.471
Human Hepatotoxicity (H-HT):	0.295
Drug-inuced Liver Injury (DILI):	0.708
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.859
Maximum Recommended Daily Dose:	0.746
Skin Sensitization:	0.923
Carcinogencity:	0.787
Eye Corrosion:	0.009
Eye Irritation:	0.046
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC230513

Natural Product ID:	NPC230513
*Common Name:**	YXNFYOIERQXPKC-UXAIKDGVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YXNFYOIERQXPKC-UXAIKDGVSA-N
Standard InCHI:	InChI=1S/C28H40O7/c1-13-9-20(35-25(32)16(13)12-29)14(2)17-5-6-18-15-10-23-28(33)24(31)21(34-23)11-22(30)27(28,4)19(15)7-8-26(17,18)3/h14-15,17-21,23-24,29,31,33H,5-12H2,1-4H3/t14-,15-,17+,18-,19-,20+,21+,23-,24-,26+,27-,28-/m0/s1
SMILES:	OCC1=C(C)C[C@@H](OC1=O)[C@H]([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[C@@H](O2)[C@@H]3O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934586
PubChem CID:	11038270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	Species	Solanaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[22098611]
NPO14874	Physalis longifolia	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	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[533799]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	10000.0	nM	PMID[533799]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[533799]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[533799]

☑ 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 NPC230513 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	290
0.1-0.2	1615
0.2-0.3	4717
0.3-0.4	7728
0.4-0.5	12363
0.5-0.6	7114
0.6-0.7	6164
0.7-0.8	2428
0.8-0.85	238
0.85-0.9	32
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.964	High Similarity	NPC42673
0.9554	High Similarity	NPC268530
0.9554	High Similarity	NPC154491
0.9469	High Similarity	NPC4021
0.9469	High Similarity	NPC159456
0.9459	High Similarity	NPC55296
0.9381	High Similarity	NPC251226
0.9279	High Similarity	NPC284915
0.9145	High Similarity	NPC120994
0.9145	High Similarity	NPC203702
0.906	High Similarity	NPC469790
0.906	High Similarity	NPC8369
0.8983	High Similarity	NPC293112
0.8974	High Similarity	NPC11895
0.8898	High Similarity	NPC81736
0.8898	High Similarity	NPC172154
0.8889	High Similarity	NPC170538
0.8889	High Similarity	NPC269642
0.8814	High Similarity	NPC469789
0.8793	High Similarity	NPC475041
0.876	High Similarity	NPC231529
0.8667	High Similarity	NPC473635
0.8644	High Similarity	NPC67569
0.8621	High Similarity	NPC58662
0.8609	High Similarity	NPC67259
0.8609	High Similarity	NPC147912
0.8596	High Similarity	NPC269530
0.8596	High Similarity	NPC476163
0.8571	High Similarity	NPC23786
0.8571	High Similarity	NPC470265
0.8559	High Similarity	NPC476961
0.8547	High Similarity	NPC113448
0.8509	High Similarity	NPC469656
0.8509	High Similarity	NPC469655
0.8509	High Similarity	NPC474846
0.85	High Similarity	NPC471392
0.85	High Similarity	NPC67251
0.8487	Intermediate Similarity	NPC46570
0.8487	Intermediate Similarity	NPC470779
0.8475	Intermediate Similarity	NPC475520
0.8462	Intermediate Similarity	NPC286528
0.8462	Intermediate Similarity	NPC20302
0.8462	Intermediate Similarity	NPC140055
0.8462	Intermediate Similarity	NPC469684
0.8462	Intermediate Similarity	NPC167606
0.8455	Intermediate Similarity	NPC473593
0.8448	Intermediate Similarity	NPC117712
0.8448	Intermediate Similarity	NPC474181
0.8435	Intermediate Similarity	NPC472002
0.8435	Intermediate Similarity	NPC285956
0.843	Intermediate Similarity	NPC476729
0.8417	Intermediate Similarity	NPC222688
0.8417	Intermediate Similarity	NPC107493
0.8393	Intermediate Similarity	NPC472655
0.839	Intermediate Similarity	NPC478206
0.839	Intermediate Similarity	NPC709
0.839	Intermediate Similarity	NPC108581
0.839	Intermediate Similarity	NPC478205
0.839	Intermediate Similarity	NPC50774
0.8376	Intermediate Similarity	NPC266728
0.8376	Intermediate Similarity	NPC72772
0.8376	Intermediate Similarity	NPC49492
0.8376	Intermediate Similarity	NPC469794
0.8376	Intermediate Similarity	NPC196931
0.8362	Intermediate Similarity	NPC25909
0.8362	Intermediate Similarity	NPC478212
0.8347	Intermediate Similarity	NPC105926
0.8347	Intermediate Similarity	NPC91693
0.8347	Intermediate Similarity	NPC18945
0.8347	Intermediate Similarity	NPC473979
0.8347	Intermediate Similarity	NPC265557
0.8319	Intermediate Similarity	NPC264954
0.8319	Intermediate Similarity	NPC9457
0.8319	Intermediate Similarity	NPC473165
0.8319	Intermediate Similarity	NPC471783
0.8305	Intermediate Similarity	NPC98249
0.8305	Intermediate Similarity	NPC470492
0.8305	Intermediate Similarity	NPC13713
0.8305	Intermediate Similarity	NPC473656
0.8305	Intermediate Similarity	NPC312824
0.8305	Intermediate Similarity	NPC183580
0.8305	Intermediate Similarity	NPC478204
0.8305	Intermediate Similarity	NPC470959
0.8305	Intermediate Similarity	NPC284068
0.8305	Intermediate Similarity	NPC470493
0.8305	Intermediate Similarity	NPC53396
0.8305	Intermediate Similarity	NPC476965
0.8293	Intermediate Similarity	NPC469757
0.8293	Intermediate Similarity	NPC471357
0.8293	Intermediate Similarity	NPC146456
0.8293	Intermediate Similarity	NPC470882
0.8293	Intermediate Similarity	NPC117702
0.8291	Intermediate Similarity	NPC326542
0.8279	Intermediate Similarity	NPC8374
0.8279	Intermediate Similarity	NPC24651
0.8279	Intermediate Similarity	NPC470922
0.8276	Intermediate Similarity	NPC207251
0.8276	Intermediate Similarity	NPC470063
0.8264	Intermediate Similarity	NPC312833
0.8261	Intermediate Similarity	NPC470496
0.825	Intermediate Similarity	NPC476962
0.825	Intermediate Similarity	NPC474370
0.825	Intermediate Similarity	NPC474585
0.8246	Intermediate Similarity	NPC273155
0.8235	Intermediate Similarity	NPC284707
0.8235	Intermediate Similarity	NPC473720
0.8235	Intermediate Similarity	NPC251310
0.823	Intermediate Similarity	NPC470587
0.8226	Intermediate Similarity	NPC473620
0.8226	Intermediate Similarity	NPC311534
0.822	Intermediate Similarity	NPC173686
0.822	Intermediate Similarity	NPC16081
0.822	Intermediate Similarity	NPC270929
0.822	Intermediate Similarity	NPC207217
0.8214	Intermediate Similarity	NPC159533
0.8205	Intermediate Similarity	NPC962
0.8205	Intermediate Similarity	NPC250109
0.8205	Intermediate Similarity	NPC122056
0.8197	Intermediate Similarity	NPC120724
0.819	Intermediate Similarity	NPC247031
0.819	Intermediate Similarity	NPC97939
0.819	Intermediate Similarity	NPC100329
0.819	Intermediate Similarity	NPC94650
0.819	Intermediate Similarity	NPC132790
0.8182	Intermediate Similarity	NPC129434
0.8167	Intermediate Similarity	NPC473636
0.8167	Intermediate Similarity	NPC312536
0.8167	Intermediate Similarity	NPC77689
0.8167	Intermediate Similarity	NPC476960
0.8167	Intermediate Similarity	NPC473839
0.8167	Intermediate Similarity	NPC211093
0.816	Intermediate Similarity	NPC86159
0.816	Intermediate Similarity	NPC469753
0.816	Intermediate Similarity	NPC471361
0.816	Intermediate Similarity	NPC10823
0.816	Intermediate Similarity	NPC471352
0.816	Intermediate Similarity	NPC469752
0.816	Intermediate Similarity	NPC180079
0.816	Intermediate Similarity	NPC251866
0.816	Intermediate Similarity	NPC284406
0.816	Intermediate Similarity	NPC17896
0.816	Intermediate Similarity	NPC70542
0.816	Intermediate Similarity	NPC89514
0.816	Intermediate Similarity	NPC469755
0.816	Intermediate Similarity	NPC9499
0.816	Intermediate Similarity	NPC6108
0.816	Intermediate Similarity	NPC476966
0.816	Intermediate Similarity	NPC469751
0.816	Intermediate Similarity	NPC219085
0.816	Intermediate Similarity	NPC469754
0.816	Intermediate Similarity	NPC471360
0.816	Intermediate Similarity	NPC471359
0.816	Intermediate Similarity	NPC471358
0.816	Intermediate Similarity	NPC197707
0.8158	Intermediate Similarity	NPC67321
0.8158	Intermediate Similarity	NPC131665
0.8158	Intermediate Similarity	NPC166993
0.8158	Intermediate Similarity	NPC255387
0.8158	Intermediate Similarity	NPC473173
0.8158	Intermediate Similarity	NPC112780
0.8158	Intermediate Similarity	NPC180744
0.8158	Intermediate Similarity	NPC469318
0.8158	Intermediate Similarity	NPC59530
0.8158	Intermediate Similarity	NPC473037
0.8158	Intermediate Similarity	NPC187435
0.8151	Intermediate Similarity	NPC473590
0.8151	Intermediate Similarity	NPC97908
0.8151	Intermediate Similarity	NPC470775
0.8151	Intermediate Similarity	NPC287343
0.8151	Intermediate Similarity	NPC122033
0.8151	Intermediate Similarity	NPC474654
0.8151	Intermediate Similarity	NPC134430
0.8151	Intermediate Similarity	NPC473968
0.8151	Intermediate Similarity	NPC470854
0.8151	Intermediate Similarity	NPC475809
0.8151	Intermediate Similarity	NPC176513
0.8151	Intermediate Similarity	NPC146432
0.8151	Intermediate Similarity	NPC470778
0.8145	Intermediate Similarity	NPC287423
0.8145	Intermediate Similarity	NPC298841
0.8145	Intermediate Similarity	NPC473253
0.8145	Intermediate Similarity	NPC42399
0.8145	Intermediate Similarity	NPC473265
0.8142	Intermediate Similarity	NPC471293
0.8142	Intermediate Similarity	NPC65523
0.8136	Intermediate Similarity	NPC45218
0.8136	Intermediate Similarity	NPC143268
0.8136	Intermediate Similarity	NPC323821
0.8136	Intermediate Similarity	NPC268238
0.813	Intermediate Similarity	NPC318135
0.8125	Intermediate Similarity	NPC295791
0.8125	Intermediate Similarity	NPC165250
0.812	Intermediate Similarity	NPC476964
0.812	Intermediate Similarity	NPC69291
0.812	Intermediate Similarity	NPC42658
0.812	Intermediate Similarity	NPC236217
0.8115	Intermediate Similarity	NPC88326
0.8115	Intermediate Similarity	NPC153700
0.811	Intermediate Similarity	NPC88668
0.8103	Intermediate Similarity	NPC5284

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 NPC230513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	1888
0.2-0.3	3840
0.3-0.4	2014
0.4-0.5	635
0.5-0.6	272
0.6-0.7	170
0.7-0.8	55
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
0.8462	Intermediate Similarity	NPD7115	Discovery
0.816	Intermediate Similarity	NPD7319	Approved
0.792	Intermediate Similarity	NPD7507	Approved
0.7863	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD7639	Approved
0.7778	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD7638	Approved
0.7699	Intermediate Similarity	NPD4225	Approved
0.7656	Intermediate Similarity	NPD7736	Approved
0.7652	Intermediate Similarity	NPD7632	Discontinued
0.7647	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7516	Approved
0.7559	Intermediate Similarity	NPD7492	Approved
0.752	Intermediate Similarity	NPD6319	Approved
0.752	Intermediate Similarity	NPD6054	Approved
0.752	Intermediate Similarity	NPD6059	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD6616	Approved
0.7458	Intermediate Similarity	NPD6008	Approved
0.7442	Intermediate Similarity	NPD7078	Approved
0.7442	Intermediate Similarity	NPD8293	Discontinued
0.7402	Intermediate Similarity	NPD6370	Approved
0.7395	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7320	Approved
0.7323	Intermediate Similarity	NPD8379	Approved
0.7323	Intermediate Similarity	NPD6016	Approved
0.7323	Intermediate Similarity	NPD8296	Approved
0.7323	Intermediate Similarity	NPD6015	Approved
0.7323	Intermediate Similarity	NPD8378	Approved
0.7323	Intermediate Similarity	NPD8033	Approved
0.7323	Intermediate Similarity	NPD8380	Approved
0.7323	Intermediate Similarity	NPD8335	Approved
0.7317	Intermediate Similarity	NPD4632	Approved
0.7311	Intermediate Similarity	NPD6402	Approved
0.7311	Intermediate Similarity	NPD7128	Approved
0.7311	Intermediate Similarity	NPD5739	Approved
0.7311	Intermediate Similarity	NPD6675	Approved
0.728	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6373	Approved
0.7273	Intermediate Similarity	NPD6372	Approved
0.7266	Intermediate Similarity	NPD5988	Approved
0.7244	Intermediate Similarity	NPD8294	Approved
0.7244	Intermediate Similarity	NPD8377	Approved
0.7236	Intermediate Similarity	NPD6053	Discontinued
0.7236	Intermediate Similarity	NPD8297	Approved
0.7209	Intermediate Similarity	NPD8328	Phase 3
0.719	Intermediate Similarity	NPD6881	Approved
0.719	Intermediate Similarity	NPD6899	Approved
0.7188	Intermediate Similarity	NPD8513	Phase 3
0.7154	Intermediate Similarity	NPD6650	Approved
0.7154	Intermediate Similarity	NPD6649	Approved
0.7131	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5697	Approved
0.7107	Intermediate Similarity	NPD5701	Approved
0.7073	Intermediate Similarity	NPD4634	Approved
0.7073	Intermediate Similarity	NPD6883	Approved
0.7073	Intermediate Similarity	NPD6371	Approved
0.7073	Intermediate Similarity	NPD7102	Approved
0.7073	Intermediate Similarity	NPD7290	Approved
0.7054	Intermediate Similarity	NPD6921	Approved
0.7054	Intermediate Similarity	NPD8516	Approved
0.7054	Intermediate Similarity	NPD8517	Approved
0.7054	Intermediate Similarity	NPD8515	Approved
0.7049	Intermediate Similarity	NPD6686	Approved
0.704	Intermediate Similarity	NPD8133	Approved
0.7016	Intermediate Similarity	NPD8130	Phase 1
0.7016	Intermediate Similarity	NPD6847	Approved
0.7016	Intermediate Similarity	NPD6617	Approved
0.7016	Intermediate Similarity	NPD6869	Approved
0.7008	Intermediate Similarity	NPD6009	Approved
0.6992	Remote Similarity	NPD6014	Approved
0.6992	Remote Similarity	NPD6033	Approved
0.6992	Remote Similarity	NPD6013	Approved
0.6992	Remote Similarity	NPD6012	Approved
0.6991	Remote Similarity	NPD5328	Approved
0.6967	Remote Similarity	NPD6412	Phase 2
0.696	Remote Similarity	NPD6882	Approved
0.6957	Remote Similarity	NPD6399	Phase 3
0.6947	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD5983	Phase 2
0.6923	Remote Similarity	NPD7503	Approved
0.6917	Remote Similarity	NPD5211	Phase 2
0.6911	Remote Similarity	NPD6011	Approved
0.6897	Remote Similarity	NPD7748	Approved
0.688	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.687	Remote Similarity	NPD8034	Phase 2
0.687	Remote Similarity	NPD7637	Suspended
0.687	Remote Similarity	NPD8035	Phase 2
0.687	Remote Similarity	NPD7515	Phase 2
0.687	Remote Similarity	NPD6079	Approved
0.6864	Remote Similarity	NPD7902	Approved
0.6864	Remote Similarity	NPD6083	Phase 2
0.6864	Remote Similarity	NPD6084	Phase 2
0.6864	Remote Similarity	NPD4755	Approved
0.6842	Remote Similarity	NPD6336	Discontinued
0.6838	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5344	Discontinued
0.6829	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5141	Approved
0.6786	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4697	Phase 3
0.675	Remote Similarity	NPD4700	Approved
0.675	Remote Similarity	NPD5285	Approved
0.675	Remote Similarity	NPD5286	Approved
0.675	Remote Similarity	NPD4696	Approved
0.6726	Remote Similarity	NPD3618	Phase 1
0.6695	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6845	Suspended
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6641	Remote Similarity	NPD7101	Approved
0.6641	Remote Similarity	NPD7100	Approved
0.6639	Remote Similarity	NPD4633	Approved
0.6639	Remote Similarity	NPD5221	Approved
0.6639	Remote Similarity	NPD5222	Approved
0.6639	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5226	Approved
0.6639	Remote Similarity	NPD5224	Approved
0.6639	Remote Similarity	NPD5225	Approved
0.6638	Remote Similarity	NPD5785	Approved
0.6614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7900	Approved
0.6609	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6114	Approved
0.6606	Remote Similarity	NPD6697	Approved
0.6606	Remote Similarity	NPD6118	Approved
0.6606	Remote Similarity	NPD6115	Approved
0.6585	Remote Similarity	NPD5174	Approved
0.6585	Remote Similarity	NPD5175	Approved
0.6583	Remote Similarity	NPD5173	Approved
0.6579	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD6335	Approved
0.6557	Remote Similarity	NPD5223	Approved
0.6555	Remote Similarity	NPD5695	Phase 3
0.6549	Remote Similarity	NPD4786	Approved
0.6541	Remote Similarity	NPD6908	Approved
0.6541	Remote Similarity	NPD6909	Approved
0.6538	Remote Similarity	NPD6868	Approved
0.6525	Remote Similarity	NPD4202	Approved
0.6496	Remote Similarity	NPD46	Approved
0.6496	Remote Similarity	NPD6698	Approved
0.6491	Remote Similarity	NPD1694	Approved
0.6489	Remote Similarity	NPD6317	Approved
0.648	Remote Similarity	NPD4767	Approved
0.648	Remote Similarity	NPD4768	Approved
0.6475	Remote Similarity	NPD6648	Approved
0.6475	Remote Similarity	NPD7260	Phase 2
0.6471	Remote Similarity	NPD6001	Approved
0.6466	Remote Similarity	NPD6672	Approved
0.6466	Remote Similarity	NPD5737	Approved
0.6466	Remote Similarity	NPD6903	Approved
0.6452	Remote Similarity	NPD4754	Approved
0.6444	Remote Similarity	NPD6067	Discontinued
0.6441	Remote Similarity	NPD7983	Approved
0.6441	Remote Similarity	NPD5693	Phase 1
0.6441	Remote Similarity	NPD6411	Approved
0.6439	Remote Similarity	NPD6314	Approved
0.6439	Remote Similarity	NPD6313	Approved
0.6435	Remote Similarity	NPD7334	Approved
0.6435	Remote Similarity	NPD6409	Approved
0.6435	Remote Similarity	NPD7521	Approved
0.6435	Remote Similarity	NPD7146	Approved
0.6435	Remote Similarity	NPD5330	Approved
0.6435	Remote Similarity	NPD6684	Approved
0.6423	Remote Similarity	NPD4159	Approved
0.6422	Remote Similarity	NPD6117	Approved
0.641	Remote Similarity	NPD4753	Phase 2
0.6379	Remote Similarity	NPD3573	Approved
0.6378	Remote Similarity	NPD4730	Approved
0.6378	Remote Similarity	NPD4729	Approved
0.6378	Remote Similarity	NPD5128	Approved
0.6372	Remote Similarity	NPD3667	Approved
0.6364	Remote Similarity	NPD6116	Phase 1
0.6333	Remote Similarity	NPD5282	Discontinued
0.633	Remote Similarity	NPD3703	Phase 2
0.6319	Remote Similarity	NPD7799	Discontinued
0.6316	Remote Similarity	NPD6695	Phase 3
0.6293	Remote Similarity	NPD5786	Approved
0.6286	Remote Similarity	NPD5956	Approved
0.6281	Remote Similarity	NPD5210	Approved
0.6281	Remote Similarity	NPD4629	Approved
0.6279	Remote Similarity	NPD5250	Approved
0.6279	Remote Similarity	NPD5249	Phase 3
0.6279	Remote Similarity	NPD5247	Approved
0.6279	Remote Similarity	NPD5251	Approved
0.6279	Remote Similarity	NPD5248	Approved
0.6271	Remote Similarity	NPD6101	Approved
0.6271	Remote Similarity	NPD6904	Approved
0.6271	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6673	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