NPASS Compound

Structure

NPC329736 OpenBabel07101718222D 35 40 0 0 1 0 0 0 0 0999 V2000 6.4456 3.8027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0399 1.8942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6601 4.0044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0676 5.8832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1199 4.0674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5167 4.9587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7927 4.1541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5177 3.5013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3149 2.5470 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 3.4146 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 1.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5347 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8649 3.8526 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3870 2.2455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 3.9024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4148 5.1582 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4870 4.8567 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3796 0.9756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1842 1.2912 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1133 6.0861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 5.8110 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6620 2.8983 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 3 24 1 0 0 0 0 4 25 1 0 0 0 0 6 7 2 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 24 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 1 1 6 0 0 0 14 15 1 0 0 0 0 15 2 1 1 0 0 0 15 23 1 0 0 0 0 16 13 1 1 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 24 1 6 0 0 0 18 25 1 6 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 28 1 6 0 0 0 20 30 1 0 0 0 0 21 26 1 0 0 0 0 21 34 1 0 0 0 0 22 28 1 1 0 0 0 22 35 1 0 0 0 0 23 31 2 0 0 0 0 23 34 1 0 0 0 0 24 27 1 1 0 0 0 25 28 1 6 0 0 0 26 5 1 6 0 0 0 26 27 1 0 0 0 0 26 32 1 0 0 0 0 27 33 1 1 0 0 0 28 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.28
Volume:	495.128
LogP:	3.027
LogD:	3.002
LogS:	-4.489
# Rotatable Bonds:	2
TPSA:	113.43
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	6.036
Fsp3:	0.893
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:	-5.156
MDCK Permeability:	2.0917461370117962e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.049
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.143
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	53.52806854248047%
Volume Distribution (VD):	0.644
Pgp-substrate:	29.871746063232422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.904
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.837
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.79
CYP3A4-substrate:	0.931

ADMET: Excretion

Clearance (CL):	9.135
Half-life (T1/2):	0.421

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.262
Drug-inuced Liver Injury (DILI):	0.293
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.589
Maximum Recommended Daily Dose:	0.728
Skin Sensitization:	0.343
Carcinogencity:	0.86
Eye Corrosion:	0.005
Eye Irritation:	0.015
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC329736

Natural Product ID:	NPC329736
*Common Name:**	Philadelphicalactone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ODFGLJQOCBLUPX-HRWIZJFJSA-N
Standard InCHI:	InChI=1S/C28H40O7/c1-14-12-21(34-23(31)15(14)2)26(5,32)27(33)11-9-17-16-13-22-28(35-22)20(30)7-6-19(29)25(28,4)18(16)8-10-24(17,27)3/h6-7,14-18,20-22,30,32-33H,8-13H2,1-5H3/t14-,15+,16-,17-,18-,20-,21?,22+,24-,25-,26-,27+,28+/m0/s1
SMILES:	C[C@@H]1[C@@H](C)CC(OC1=O)[C@@]([C@@]1(O)CC[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[C@@H]3O)O2)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507728
PubChem CID:	11038269
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
NPO10122	Deprea subtriflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932130]
NPO10122	Deprea subtriflora	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	1
Others	2

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	0.04	uM	PMID[539086]
NPT27	Others	Unspecified		IC50	=	470.0	nM	PMID[539086]
NPT2	Others	Unspecified		Ratio	=	11.8	n.a.	PMID[539086]

☑ 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 NPC329736 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	241
0.1-0.2	1410
0.2-0.3	4400
0.3-0.4	8642
0.4-0.5	12355
0.5-0.6	6551
0.6-0.7	6172
0.7-0.8	2638
0.8-0.85	205
0.85-0.9	69
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC61520
0.9815	High Similarity	NPC270929
0.9375	High Similarity	NPC264954
0.931	High Similarity	NPC473253
0.9292	High Similarity	NPC474370
0.9196	High Similarity	NPC286528
0.9196	High Similarity	NPC470492
0.9196	High Similarity	NPC167606
0.9196	High Similarity	NPC140055
0.9196	High Similarity	NPC20302
0.9153	High Similarity	NPC470880
0.913	High Similarity	NPC153700
0.913	High Similarity	NPC88326
0.9115	High Similarity	NPC709
0.9115	High Similarity	NPC50774
0.9052	High Similarity	NPC469789
0.9035	High Similarity	NPC473203
0.9027	High Similarity	NPC312824
0.9027	High Similarity	NPC470493
0.9027	High Similarity	NPC183580
0.8983	High Similarity	NPC473265
0.8983	High Similarity	NPC470882
0.8974	High Similarity	NPC172154
0.8974	High Similarity	NPC8369
0.8974	High Similarity	NPC81736
0.8974	High Similarity	NPC8374
0.8929	High Similarity	NPC122056
0.8898	High Similarity	NPC293112
0.8889	High Similarity	NPC11895
0.8879	High Similarity	NPC470878
0.8879	High Similarity	NPC67569
0.8879	High Similarity	NPC473256
0.886	High Similarity	NPC471854
0.886	High Similarity	NPC476965
0.886	High Similarity	NPC470959
0.885	High Similarity	NPC67259
0.885	High Similarity	NPC147912
0.8824	High Similarity	NPC287423
0.8803	High Similarity	NPC23786
0.8803	High Similarity	NPC170538
0.8803	High Similarity	NPC470265
0.8783	High Similarity	NPC186525
0.8739	High Similarity	NPC475941
0.8739	High Similarity	NPC474901
0.8729	High Similarity	NPC204812
0.8718	High Similarity	NPC46570
0.8707	High Similarity	NPC473274
0.8707	High Similarity	NPC476960
0.8684	High Similarity	NPC284915
0.8673	High Similarity	NPC475970
0.8673	High Similarity	NPC191620
0.8655	High Similarity	NPC32868
0.8655	High Similarity	NPC473255
0.8655	High Similarity	NPC241456
0.8655	High Similarity	NPC470494
0.8655	High Similarity	NPC3381
0.8644	High Similarity	NPC107493
0.8644	High Similarity	NPC269642
0.8632	High Similarity	NPC476961
0.8621	High Similarity	NPC473720
0.8621	High Similarity	NPC311554
0.8621	High Similarity	NPC257457
0.8596	High Similarity	NPC250109
0.8596	High Similarity	NPC317210
0.8595	High Similarity	NPC473620
0.8584	High Similarity	NPC470960
0.8583	High Similarity	NPC473635
0.8571	High Similarity	NPC214644
0.8571	High Similarity	NPC41405
0.8547	High Similarity	NPC475041
0.8547	High Similarity	NPC473270
0.8545	High Similarity	NPC75531
0.8545	High Similarity	NPC149124
0.8534	High Similarity	NPC243065
0.8525	High Similarity	NPC231529
0.8512	High Similarity	NPC305496
0.8509	High Similarity	NPC476163
0.8496	Intermediate Similarity	NPC37116
0.8496	Intermediate Similarity	NPC76084
0.8475	Intermediate Similarity	NPC476962
0.8448	Intermediate Similarity	NPC64318
0.8443	Intermediate Similarity	NPC473888
0.8435	Intermediate Similarity	NPC962
0.8421	Intermediate Similarity	NPC474315
0.8421	Intermediate Similarity	NPC470961
0.8417	Intermediate Similarity	NPC473979
0.8417	Intermediate Similarity	NPC120724
0.8393	Intermediate Similarity	NPC473284
0.8393	Intermediate Similarity	NPC144459
0.839	Intermediate Similarity	NPC475520
0.8387	Intermediate Similarity	NPC231240
0.8376	Intermediate Similarity	NPC218970
0.8376	Intermediate Similarity	NPC239273
0.8374	Intermediate Similarity	NPC473593
0.8364	Intermediate Similarity	NPC136289
0.8364	Intermediate Similarity	NPC477915
0.8364	Intermediate Similarity	NPC473424
0.8362	Intermediate Similarity	NPC243354
0.8348	Intermediate Similarity	NPC475524
0.8348	Intermediate Similarity	NPC100267
0.8348	Intermediate Similarity	NPC207251
0.8333	Intermediate Similarity	NPC29133
0.832	Intermediate Similarity	NPC316915
0.8319	Intermediate Similarity	NPC154491
0.8319	Intermediate Similarity	NPC79579
0.8319	Intermediate Similarity	NPC268530
0.8319	Intermediate Similarity	NPC177064
0.8305	Intermediate Similarity	NPC153440
0.8304	Intermediate Similarity	NPC149047
0.8304	Intermediate Similarity	NPC60681
0.8293	Intermediate Similarity	NPC311534
0.8291	Intermediate Similarity	NPC298278
0.8291	Intermediate Similarity	NPC266728
0.8291	Intermediate Similarity	NPC148458
0.8291	Intermediate Similarity	NPC49492
0.8291	Intermediate Similarity	NPC190286
0.8288	Intermediate Similarity	NPC26478
0.8288	Intermediate Similarity	NPC264048
0.8288	Intermediate Similarity	NPC475050
0.8288	Intermediate Similarity	NPC311612
0.8276	Intermediate Similarity	NPC255017
0.8276	Intermediate Similarity	NPC194100
0.8273	Intermediate Similarity	NPC476897
0.8273	Intermediate Similarity	NPC476223
0.8273	Intermediate Similarity	NPC476240
0.8273	Intermediate Similarity	NPC224720
0.8273	Intermediate Similarity	NPC81530
0.8261	Intermediate Similarity	NPC474229
0.825	Intermediate Similarity	NPC4021
0.825	Intermediate Similarity	NPC470921
0.825	Intermediate Similarity	NPC159456
0.8246	Intermediate Similarity	NPC475065
0.824	Intermediate Similarity	NPC471855
0.8235	Intermediate Similarity	NPC42673
0.8235	Intermediate Similarity	NPC5292
0.823	Intermediate Similarity	NPC185
0.823	Intermediate Similarity	NPC44063
0.823	Intermediate Similarity	NPC329048
0.823	Intermediate Similarity	NPC9457
0.823	Intermediate Similarity	NPC83744
0.823	Intermediate Similarity	NPC220974
0.823	Intermediate Similarity	NPC471783
0.823	Intermediate Similarity	NPC220229
0.823	Intermediate Similarity	NPC91034
0.823	Intermediate Similarity	NPC475060
0.823	Intermediate Similarity	NPC330011
0.823	Intermediate Similarity	NPC477916
0.8214	Intermediate Similarity	NPC204833
0.8214	Intermediate Similarity	NPC137657
0.8214	Intermediate Similarity	NPC209502
0.8205	Intermediate Similarity	NPC326542
0.8205	Intermediate Similarity	NPC470953
0.8198	Intermediate Similarity	NPC87351
0.8198	Intermediate Similarity	NPC185530
0.8197	Intermediate Similarity	NPC469790
0.819	Intermediate Similarity	NPC269530
0.819	Intermediate Similarity	NPC71348
0.8182	Intermediate Similarity	NPC222688
0.8182	Intermediate Similarity	NPC28532
0.8182	Intermediate Similarity	NPC476274
0.8174	Intermediate Similarity	NPC473627
0.8174	Intermediate Similarity	NPC5284
0.8174	Intermediate Similarity	NPC197428
0.8174	Intermediate Similarity	NPC239097
0.8167	Intermediate Similarity	NPC251226
0.8167	Intermediate Similarity	NPC474585
0.816	Intermediate Similarity	NPC220757
0.816	Intermediate Similarity	NPC196921
0.816	Intermediate Similarity	NPC173347
0.8158	Intermediate Similarity	NPC472825
0.8158	Intermediate Similarity	NPC473482
0.8158	Intermediate Similarity	NPC65941
0.8158	Intermediate Similarity	NPC217201
0.8158	Intermediate Similarity	NPC329417
0.8158	Intermediate Similarity	NPC475418
0.8158	Intermediate Similarity	NPC318363
0.8154	Intermediate Similarity	NPC473396
0.8151	Intermediate Similarity	NPC113448
0.8151	Intermediate Similarity	NPC251310
0.8142	Intermediate Similarity	NPC171137
0.8142	Intermediate Similarity	NPC152695
0.8142	Intermediate Similarity	NPC202167
0.8142	Intermediate Similarity	NPC296945
0.8142	Intermediate Similarity	NPC85829
0.8142	Intermediate Similarity	NPC319077
0.8142	Intermediate Similarity	NPC97202
0.8142	Intermediate Similarity	NPC50692
0.8142	Intermediate Similarity	NPC49958
0.8142	Intermediate Similarity	NPC260268
0.8142	Intermediate Similarity	NPC214264
0.8142	Intermediate Similarity	NPC302607
0.8142	Intermediate Similarity	NPC150531
0.8142	Intermediate Similarity	NPC476027
0.8142	Intermediate Similarity	NPC48733
0.814	Intermediate Similarity	NPC473233
0.8136	Intermediate Similarity	NPC176840
0.813	Intermediate Similarity	NPC47113
0.813	Intermediate Similarity	NPC159499
0.813	Intermediate Similarity	NPC174367
0.8125	Intermediate Similarity	NPC470310

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 NPC329736 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1611
0.2-0.3	3779
0.3-0.4	2350
0.4-0.5	699
0.5-0.6	209
0.6-0.7	168
0.7-0.8	121
0.8-0.85	6
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9196	High Similarity	NPD7115	Discovery
0.8348	Intermediate Similarity	NPD8297	Approved
0.8319	Intermediate Similarity	NPD6899	Approved
0.8319	Intermediate Similarity	NPD6881	Approved
0.8261	Intermediate Similarity	NPD6649	Approved
0.8261	Intermediate Similarity	NPD6650	Approved
0.823	Intermediate Similarity	NPD5697	Approved
0.8174	Intermediate Similarity	NPD7290	Approved
0.8174	Intermediate Similarity	NPD6883	Approved
0.8174	Intermediate Similarity	NPD7102	Approved
0.8167	Intermediate Similarity	NPD6319	Approved
0.8142	Intermediate Similarity	NPD6675	Approved
0.8142	Intermediate Similarity	NPD7128	Approved
0.8142	Intermediate Similarity	NPD6402	Approved
0.8142	Intermediate Similarity	NPD5739	Approved
0.8103	Intermediate Similarity	NPD6869	Approved
0.8103	Intermediate Similarity	NPD6847	Approved
0.8103	Intermediate Similarity	NPD8130	Phase 1
0.8103	Intermediate Similarity	NPD6617	Approved
0.8087	Intermediate Similarity	NPD6014	Approved
0.8087	Intermediate Similarity	NPD6012	Approved
0.8087	Intermediate Similarity	NPD6013	Approved
0.8087	Intermediate Similarity	NPD6373	Approved
0.8087	Intermediate Similarity	NPD6372	Approved
0.8036	Intermediate Similarity	NPD5211	Phase 2
0.8034	Intermediate Similarity	NPD6882	Approved
0.8	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD7320	Approved
0.7966	Intermediate Similarity	NPD4632	Approved
0.7913	Intermediate Similarity	NPD5701	Approved
0.7903	Intermediate Similarity	NPD7492	Approved
0.7895	Intermediate Similarity	NPD5141	Approved
0.7869	Intermediate Similarity	NPD6054	Approved
0.7863	Intermediate Similarity	NPD4634	Approved
0.7857	Intermediate Similarity	NPD5285	Approved
0.7857	Intermediate Similarity	NPD5286	Approved
0.7857	Intermediate Similarity	NPD4696	Approved
0.7857	Intermediate Similarity	NPD7736	Approved
0.784	Intermediate Similarity	NPD6616	Approved
0.7826	Intermediate Similarity	NPD6008	Approved
0.7795	Intermediate Similarity	NPD7319	Approved
0.7778	Intermediate Similarity	NPD7078	Approved
0.7768	Intermediate Similarity	NPD4225	Approved
0.7742	Intermediate Similarity	NPD6370	Approved
0.7719	Intermediate Similarity	NPD5225	Approved
0.7719	Intermediate Similarity	NPD5224	Approved
0.7719	Intermediate Similarity	NPD5226	Approved
0.7719	Intermediate Similarity	NPD4633	Approved
0.7706	Intermediate Similarity	NPD6079	Approved
0.7698	Intermediate Similarity	NPD7507	Approved
0.768	Intermediate Similarity	NPD7604	Phase 2
0.7679	Intermediate Similarity	NPD6083	Phase 2
0.7679	Intermediate Similarity	NPD6084	Phase 2
0.7679	Intermediate Similarity	NPD4755	Approved
0.7661	Intermediate Similarity	NPD6016	Approved
0.7661	Intermediate Similarity	NPD6015	Approved
0.7652	Intermediate Similarity	NPD5174	Approved
0.7652	Intermediate Similarity	NPD5175	Approved
0.7647	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7101	Approved
0.7642	Intermediate Similarity	NPD7100	Approved
0.7632	Intermediate Similarity	NPD5223	Approved
0.7623	Intermediate Similarity	NPD6009	Approved
0.76	Intermediate Similarity	NPD5988	Approved
0.7581	Intermediate Similarity	NPD6059	Approved
0.7561	Intermediate Similarity	NPD6335	Approved
0.7544	Intermediate Similarity	NPD4700	Approved
0.7541	Intermediate Similarity	NPD6274	Approved
0.7523	Intermediate Similarity	NPD5328	Approved
0.752	Intermediate Similarity	NPD5983	Phase 2
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8293	Discontinued
0.748	Intermediate Similarity	NPD6317	Approved
0.7477	Intermediate Similarity	NPD6399	Phase 3
0.7458	Intermediate Similarity	NPD6412	Phase 2
0.7456	Intermediate Similarity	NPD5696	Approved
0.7455	Intermediate Similarity	NPD5785	Approved
0.7434	Intermediate Similarity	NPD5221	Approved
0.7434	Intermediate Similarity	NPD5222	Approved
0.7434	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD6336	Discontinued
0.7419	Intermediate Similarity	NPD6313	Approved
0.7419	Intermediate Similarity	NPD6314	Approved
0.7395	Intermediate Similarity	NPD4729	Approved
0.7395	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD4730	Approved
0.7391	Intermediate Similarity	NPD7639	Approved
0.7391	Intermediate Similarity	NPD7640	Approved
0.7381	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5173	Approved
0.7345	Intermediate Similarity	NPD4629	Approved
0.7345	Intermediate Similarity	NPD5695	Phase 3
0.7345	Intermediate Similarity	NPD5210	Approved
0.7339	Intermediate Similarity	NPD3573	Approved
0.7321	Intermediate Similarity	NPD4202	Approved
0.7315	Intermediate Similarity	NPD5363	Approved
0.7304	Intermediate Similarity	NPD7638	Approved
0.7281	Intermediate Similarity	NPD4697	Phase 3
0.7273	Intermediate Similarity	NPD5247	Approved
0.7273	Intermediate Similarity	NPD5249	Phase 3
0.7273	Intermediate Similarity	NPD6371	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5251	Approved
0.7273	Intermediate Similarity	NPD5250	Approved
0.7273	Intermediate Similarity	NPD5248	Approved
0.7266	Intermediate Similarity	NPD8328	Phase 3
0.7258	Intermediate Similarity	NPD6868	Approved
0.7257	Intermediate Similarity	NPD7748	Approved
0.725	Intermediate Similarity	NPD5128	Approved
0.7248	Intermediate Similarity	NPD7334	Approved
0.7248	Intermediate Similarity	NPD6684	Approved
0.7248	Intermediate Similarity	NPD7521	Approved
0.7248	Intermediate Similarity	NPD7146	Approved
0.7248	Intermediate Similarity	NPD6409	Approved
0.7248	Intermediate Similarity	NPD3618	Phase 1
0.7248	Intermediate Similarity	NPD5330	Approved
0.7248	Intermediate Similarity	NPD5786	Approved
0.7248	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7503	Approved
0.7244	Intermediate Similarity	NPD6909	Approved
0.7244	Intermediate Similarity	NPD6908	Approved
0.7232	Intermediate Similarity	NPD7515	Phase 2
0.7232	Intermediate Similarity	NPD6411	Approved
0.7227	Intermediate Similarity	NPD4768	Approved
0.7227	Intermediate Similarity	NPD4767	Approved
0.7217	Intermediate Similarity	NPD7902	Approved
0.7213	Intermediate Similarity	NPD5215	Approved
0.7213	Intermediate Similarity	NPD5217	Approved
0.7213	Intermediate Similarity	NPD5216	Approved
0.7207	Intermediate Similarity	NPD4753	Phase 2
0.7203	Intermediate Similarity	NPD4754	Approved
0.719	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7328	Approved
0.7143	Intermediate Similarity	NPD7327	Approved
0.7131	Intermediate Similarity	NPD5135	Approved
0.7131	Intermediate Similarity	NPD5169	Approved
0.7131	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6903	Approved
0.7109	Intermediate Similarity	NPD8033	Approved
0.7105	Intermediate Similarity	NPD6001	Approved
0.7087	Intermediate Similarity	NPD7516	Approved
0.708	Intermediate Similarity	NPD5281	Approved
0.708	Intermediate Similarity	NPD5284	Approved
0.7073	Intermediate Similarity	NPD5127	Approved
0.7064	Intermediate Similarity	NPD4786	Approved
0.7064	Intermediate Similarity	NPD3665	Phase 1
0.7064	Intermediate Similarity	NPD3666	Approved
0.7064	Intermediate Similarity	NPD3133	Approved
0.7054	Intermediate Similarity	NPD6904	Approved
0.7054	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6673	Approved
0.7054	Intermediate Similarity	NPD6080	Approved
0.7054	Intermediate Similarity	NPD6101	Approved
0.7045	Intermediate Similarity	NPD6033	Approved
0.7037	Intermediate Similarity	NPD4269	Approved
0.7037	Intermediate Similarity	NPD4270	Approved
0.7031	Intermediate Similarity	NPD8377	Approved
0.7031	Intermediate Similarity	NPD8294	Approved
0.7018	Intermediate Similarity	NPD5778	Approved
0.7018	Intermediate Similarity	NPD5779	Approved
0.7016	Intermediate Similarity	NPD6053	Discontinued
0.6992	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8513	Phase 3
0.6977	Remote Similarity	NPD8379	Approved
0.6977	Remote Similarity	NPD8296	Approved
0.6977	Remote Similarity	NPD8378	Approved
0.6977	Remote Similarity	NPD8517	Approved
0.6977	Remote Similarity	NPD8515	Approved
0.6977	Remote Similarity	NPD8335	Approved
0.6977	Remote Similarity	NPD8516	Approved
0.6977	Remote Similarity	NPD8380	Approved
0.6967	Remote Similarity	NPD6686	Approved
0.6964	Remote Similarity	NPD6672	Approved
0.6964	Remote Similarity	NPD5737	Approved
0.6957	Remote Similarity	NPD7900	Approved
0.6957	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5369	Approved
0.693	Remote Similarity	NPD5693	Phase 1
0.693	Remote Similarity	NPD8034	Phase 2
0.693	Remote Similarity	NPD8035	Phase 2
0.693	Remote Similarity	NPD7637	Suspended
0.6929	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5167	Approved
0.6881	Remote Similarity	NPD3667	Approved
0.6881	Remote Similarity	NPD4221	Approved
0.6881	Remote Similarity	NPD4223	Phase 3
0.6852	Remote Similarity	NPD4252	Approved
0.6847	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5329	Approved
0.6842	Remote Similarity	NPD5207	Approved
0.6833	Remote Similarity	NPD7632	Discontinued
0.6829	Remote Similarity	NPD5168	Approved
0.6814	Remote Similarity	NPD5208	Approved
0.6786	Remote Similarity	NPD6098	Approved
0.6786	Remote Similarity	NPD5690	Phase 2
0.6783	Remote Similarity	NPD5694	Approved
0.6783	Remote Similarity	NPD6050	Approved
0.6774	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4197	Approved
0.6752	Remote Similarity	NPD1698	Clinical (unspecified phase)

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