NPASS Compound

Structure

NPC473203 OpenBabel07101718192D 38 43 0 0 1 0 0 0 0 0999 V2000 -8.6257 1.3567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2875 2.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2900 -3.8803 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0025 -1.2702 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 -3.4641 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 -7.3386 0.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6476 1.1488 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9785 1.8920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3119 -3.6723 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 -2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0733 -1.1691 0.0000 C 0 0 1 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 -6.3604 -0.0102 0.0000 C 0 0 1 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 -3.6720 -1.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0003 1.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 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 -6.0514 -0.9612 0.0000 C 0 0 1 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 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6428 -4.4155 0.0000 O 0 0 0 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 -5.3312 2.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2593 -1.9394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4696 -1.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0029 -2.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6913 0.7330 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 17 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 7 8 2 0 0 0 0 7 10 1 0 0 0 0 8 21 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 11 26 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 13 23 1 0 0 0 0 14 20 1 0 0 0 0 14 24 1 0 0 0 0 15 1 1 6 0 0 0 15 16 1 0 0 0 0 16 2 1 1 0 0 0 16 25 1 0 0 0 0 17 31 2 0 0 0 0 17 36 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 6 0 0 0 19 30 1 1 0 0 0 20 26 1 6 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 21 32 2 0 0 0 0 22 28 1 6 0 0 0 22 37 1 0 0 0 0 23 29 1 6 0 0 0 23 38 1 0 0 0 0 24 30 1 1 0 0 0 24 36 1 0 0 0 0 25 33 2 0 0 0 0 25 37 1 0 0 0 0 26 30 1 6 0 0 0 27 29 1 6 0 0 0 28 6 1 6 0 0 0 28 34 1 0 0 0 0 29 10 1 1 0 0 0 29 38 1 0 0 0 0 30 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.29
Volume:	535.873
LogP:	3.25
LogD:	1.624
LogS:	-4.837
# Rotatable Bonds:	4
TPSA:	122.66
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.324
Synthetic Accessibility Score:	6.333
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.147
MDCK Permeability:	6.954724085517228e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.426
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.771
30% Bioavailability (F30%):	0.919

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.955
Plasma Protein Binding (PPB):	32.15317916870117%
Volume Distribution (VD):	0.849
Pgp-substrate:	40.5897331237793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.58
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.631
CYP3A4-substrate:	0.393

ADMET: Excretion

Clearance (CL):	4.989
Half-life (T1/2):	0.425

ADMET: Toxicity

hERG Blockers:	0.255
Human Hepatotoxicity (H-HT):	0.505
Drug-inuced Liver Injury (DILI):	0.56
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.517
Carcinogencity:	0.813
Eye Corrosion:	0.022
Eye Irritation:	0.089
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC473203

Natural Product ID:	NPC473203
*Common Name:**	TZUFAJFRNMHLPB-DLMXSQBOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TZUFAJFRNMHLPB-DLMXSQBOSA-N
Standard InCHI:	InChI=1S/C30H42O8/c1-15-12-22(37-25(33)16(15)2)28(6,34)20-14-24(36-17(3)31)30(35)19-13-23-29(38-23)10-7-8-21(32)27(29,5)18(19)9-11-26(20,30)4/h7-8,15-16,18-20,22-24,34-35H,9-14H2,1-6H3/t15-,16+,18-,19+,20-,22-,23+,24-,26+,27-,28+,29+,30+/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@H]([C@@]2([C@@]1(O)[C@@H]1C[C@H]3O[C@]43[C@]([C@H]1CC2)(C)C(=O)C=CC4)C)[C@]([C@@H]1C[C@H](C)[C@H](C(=O)O1)C)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3634982
PubChem CID:	n.a.
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
NPO33275	physalis neomexicana	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26492982]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	1700.0	nM	PMID[517492]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	6300.0	nM	PMID[517492]

☑ 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 NPC473203 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	262
0.1-0.2	1578
0.2-0.3	5103
0.3-0.4	8875
0.4-0.5	11822
0.5-0.6	6319
0.6-0.7	5919
0.7-0.8	2547
0.8-0.85	210
0.85-0.9	51
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9237	High Similarity	NPC470880
0.9224	High Similarity	NPC473255
0.9123	High Similarity	NPC61520
0.9068	High Similarity	NPC473265
0.9068	High Similarity	NPC473253
0.9035	High Similarity	NPC329736
0.8908	High Similarity	NPC470882
0.8908	High Similarity	NPC305496
0.8908	High Similarity	NPC287423
0.886	High Similarity	NPC270929
0.8824	High Similarity	NPC473635
0.8814	High Similarity	NPC469789
0.8729	High Similarity	NPC269642
0.8729	High Similarity	NPC23786
0.8729	High Similarity	NPC170538
0.8729	High Similarity	NPC470265
0.8707	High Similarity	NPC473720
0.8678	High Similarity	NPC473620
0.8667	High Similarity	NPC293112
0.8655	High Similarity	NPC11895
0.8655	High Similarity	NPC204812
0.8644	High Similarity	NPC67569
0.8632	High Similarity	NPC476960
0.8609	High Similarity	NPC243354
0.8607	High Similarity	NPC231529
0.8584	High Similarity	NPC197428
0.8583	High Similarity	NPC32868
0.8583	High Similarity	NPC172154
0.8583	High Similarity	NPC8369
0.8583	High Similarity	NPC81736
0.8583	High Similarity	NPC241456
0.8583	High Similarity	NPC8374
0.8559	High Similarity	NPC474370
0.8559	High Similarity	NPC476961
0.8547	High Similarity	NPC118638
0.8534	High Similarity	NPC190286
0.8534	High Similarity	NPC298278
0.8534	High Similarity	NPC270958
0.8522	High Similarity	NPC962
0.8522	High Similarity	NPC250109
0.8522	High Similarity	NPC194100
0.8512	High Similarity	NPC47113
0.8512	High Similarity	NPC174367
0.8509	High Similarity	NPC474229
0.85	High Similarity	NPC120724
0.8487	Intermediate Similarity	NPC470921
0.8487	Intermediate Similarity	NPC46570
0.8487	Intermediate Similarity	NPC310511
0.8475	Intermediate Similarity	NPC5292
0.8475	Intermediate Similarity	NPC475520
0.8475	Intermediate Similarity	NPC264954
0.8475	Intermediate Similarity	NPC475041
0.8448	Intermediate Similarity	NPC471398
0.8435	Intermediate Similarity	NPC71348
0.8417	Intermediate Similarity	NPC88326
0.8417	Intermediate Similarity	NPC153700
0.8417	Intermediate Similarity	NPC107493
0.8403	Intermediate Similarity	NPC79579
0.839	Intermediate Similarity	NPC153440
0.839	Intermediate Similarity	NPC709
0.839	Intermediate Similarity	NPC50774
0.8376	Intermediate Similarity	NPC266728
0.8376	Intermediate Similarity	NPC49492
0.8374	Intermediate Similarity	NPC311534
0.8362	Intermediate Similarity	NPC317210
0.8362	Intermediate Similarity	NPC52634
0.8362	Intermediate Similarity	NPC320118
0.8362	Intermediate Similarity	NPC194273
0.8362	Intermediate Similarity	NPC255017
0.8362	Intermediate Similarity	NPC202889
0.8348	Intermediate Similarity	NPC471243
0.8333	Intermediate Similarity	NPC41405
0.8333	Intermediate Similarity	NPC477046
0.8333	Intermediate Similarity	NPC102822
0.8333	Intermediate Similarity	NPC474242
0.832	Intermediate Similarity	NPC231240
0.832	Intermediate Similarity	NPC471855
0.8319	Intermediate Similarity	NPC469488
0.8305	Intermediate Similarity	NPC470492
0.8305	Intermediate Similarity	NPC97908
0.8305	Intermediate Similarity	NPC167606
0.8305	Intermediate Similarity	NPC286528
0.8305	Intermediate Similarity	NPC20302
0.8305	Intermediate Similarity	NPC470854
0.8305	Intermediate Similarity	NPC474654
0.8305	Intermediate Similarity	NPC470959
0.8305	Intermediate Similarity	NPC287343
0.8305	Intermediate Similarity	NPC476965
0.8305	Intermediate Similarity	NPC122033
0.8305	Intermediate Similarity	NPC218970
0.8305	Intermediate Similarity	NPC140055
0.8304	Intermediate Similarity	NPC96268
0.8291	Intermediate Similarity	NPC473898
0.8288	Intermediate Similarity	NPC22388
0.8279	Intermediate Similarity	NPC469790
0.8276	Intermediate Similarity	NPC205534
0.8276	Intermediate Similarity	NPC170487
0.8276	Intermediate Similarity	NPC280782
0.8276	Intermediate Similarity	NPC152117
0.8276	Intermediate Similarity	NPC234042
0.8276	Intermediate Similarity	NPC474927
0.8264	Intermediate Similarity	NPC65858
0.8261	Intermediate Similarity	NPC76084
0.8254	Intermediate Similarity	NPC316915
0.825	Intermediate Similarity	NPC251226
0.825	Intermediate Similarity	NPC474585
0.824	Intermediate Similarity	NPC173347
0.8235	Intermediate Similarity	NPC470420
0.8235	Intermediate Similarity	NPC17772
0.8235	Intermediate Similarity	NPC297179
0.8231	Intermediate Similarity	NPC473396
0.823	Intermediate Similarity	NPC278628
0.823	Intermediate Similarity	NPC231530
0.823	Intermediate Similarity	NPC96377
0.8226	Intermediate Similarity	NPC473888
0.822	Intermediate Similarity	NPC40632
0.822	Intermediate Similarity	NPC328374
0.822	Intermediate Similarity	NPC96312
0.822	Intermediate Similarity	NPC176840
0.822	Intermediate Similarity	NPC251236
0.8217	Intermediate Similarity	NPC473233
0.8214	Intermediate Similarity	NPC159442
0.8205	Intermediate Similarity	NPC208998
0.8205	Intermediate Similarity	NPC7921
0.8205	Intermediate Similarity	NPC178981
0.8205	Intermediate Similarity	NPC471252
0.8205	Intermediate Similarity	NPC49451
0.8197	Intermediate Similarity	NPC267822
0.8197	Intermediate Similarity	NPC473979
0.8197	Intermediate Similarity	NPC43252
0.8197	Intermediate Similarity	NPC135038
0.819	Intermediate Similarity	NPC214797
0.819	Intermediate Similarity	NPC472003
0.819	Intermediate Similarity	NPC231589
0.819	Intermediate Similarity	NPC470960
0.819	Intermediate Similarity	NPC118860
0.819	Intermediate Similarity	NPC213320
0.8182	Intermediate Similarity	NPC159456
0.8182	Intermediate Similarity	NPC477854
0.8182	Intermediate Similarity	NPC4021
0.8174	Intermediate Similarity	NPC241927
0.8174	Intermediate Similarity	NPC274827
0.8174	Intermediate Similarity	NPC258543
0.8167	Intermediate Similarity	NPC305260
0.8167	Intermediate Similarity	NPC319570
0.8167	Intermediate Similarity	NPC470777
0.8167	Intermediate Similarity	NPC270850
0.8167	Intermediate Similarity	NPC472667
0.816	Intermediate Similarity	NPC473593
0.816	Intermediate Similarity	NPC471407
0.816	Intermediate Similarity	NPC476966
0.8151	Intermediate Similarity	NPC470493
0.8151	Intermediate Similarity	NPC312824
0.8151	Intermediate Similarity	NPC183580
0.8151	Intermediate Similarity	NPC471854
0.8151	Intermediate Similarity	NPC470171
0.8151	Intermediate Similarity	NPC239273
0.8145	Intermediate Similarity	NPC42399
0.8142	Intermediate Similarity	NPC255309
0.8142	Intermediate Similarity	NPC29705
0.8136	Intermediate Similarity	NPC473798
0.8136	Intermediate Similarity	NPC470953
0.813	Intermediate Similarity	NPC169818
0.812	Intermediate Similarity	NPC269530
0.812	Intermediate Similarity	NPC473397
0.8115	Intermediate Similarity	NPC222688
0.8115	Intermediate Similarity	NPC156789
0.8115	Intermediate Similarity	NPC28532
0.8103	Intermediate Similarity	NPC5284
0.8103	Intermediate Similarity	NPC474567
0.8103	Intermediate Similarity	NPC320383
0.8103	Intermediate Similarity	NPC474786
0.8103	Intermediate Similarity	NPC137104
0.8103	Intermediate Similarity	NPC471093
0.8103	Intermediate Similarity	NPC6206
0.8103	Intermediate Similarity	NPC235077
0.8099	Intermediate Similarity	NPC241192
0.8099	Intermediate Similarity	NPC109973
0.8099	Intermediate Similarity	NPC268530
0.8099	Intermediate Similarity	NPC154491
0.8099	Intermediate Similarity	NPC476962
0.8099	Intermediate Similarity	NPC471406
0.8087	Intermediate Similarity	NPC293850
0.8087	Intermediate Similarity	NPC273155
0.8087	Intermediate Similarity	NPC470269
0.8087	Intermediate Similarity	NPC94529
0.8083	Intermediate Similarity	NPC311554
0.8083	Intermediate Similarity	NPC204552
0.8083	Intermediate Similarity	NPC251310
0.8083	Intermediate Similarity	NPC475632
0.8083	Intermediate Similarity	NPC186525
0.8083	Intermediate Similarity	NPC239293
0.8083	Intermediate Similarity	NPC188667
0.8083	Intermediate Similarity	NPC86020
0.8083	Intermediate Similarity	NPC257457
0.8083	Intermediate Similarity	NPC113448
0.808	Intermediate Similarity	NPC245094
0.807	Intermediate Similarity	NPC102352
0.807	Intermediate Similarity	NPC470587
0.8067	Intermediate Similarity	NPC134869

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 NPC473203 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	1821
0.2-0.3	3963
0.3-0.4	2048
0.4-0.5	587
0.5-0.6	249
0.6-0.7	152
0.7-0.8	103
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8718	High Similarity	NPD6319	Approved
0.8393	Intermediate Similarity	NPD6008	Approved
0.8362	Intermediate Similarity	NPD4632	Approved
0.8305	Intermediate Similarity	NPD7115	Discovery
0.8279	Intermediate Similarity	NPD7492	Approved
0.8276	Intermediate Similarity	NPD8297	Approved
0.825	Intermediate Similarity	NPD6054	Approved
0.8226	Intermediate Similarity	NPD7736	Approved
0.8211	Intermediate Similarity	NPD6616	Approved
0.819	Intermediate Similarity	NPD6650	Approved
0.819	Intermediate Similarity	NPD6649	Approved
0.8145	Intermediate Similarity	NPD7078	Approved
0.8115	Intermediate Similarity	NPD6370	Approved
0.8103	Intermediate Similarity	NPD4634	Approved
0.8087	Intermediate Similarity	NPD6881	Approved
0.8087	Intermediate Similarity	NPD6899	Approved
0.8049	Intermediate Similarity	NPD7604	Phase 2
0.8033	Intermediate Similarity	NPD6015	Approved
0.8033	Intermediate Similarity	NPD6016	Approved
0.8017	Intermediate Similarity	NPD6373	Approved
0.8017	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD6009	Approved
0.8	Intermediate Similarity	NPD5697	Approved
0.7967	Intermediate Similarity	NPD5988	Approved
0.7966	Intermediate Similarity	NPD6882	Approved
0.7951	Intermediate Similarity	NPD6059	Approved
0.7949	Intermediate Similarity	NPD7290	Approved
0.7949	Intermediate Similarity	NPD7102	Approved
0.7949	Intermediate Similarity	NPD6883	Approved
0.7931	Intermediate Similarity	NPD6011	Approved
0.7913	Intermediate Similarity	NPD6675	Approved
0.7913	Intermediate Similarity	NPD6402	Approved
0.7913	Intermediate Similarity	NPD7128	Approved
0.7913	Intermediate Similarity	NPD5739	Approved
0.7886	Intermediate Similarity	NPD5983	Phase 2
0.7881	Intermediate Similarity	NPD6617	Approved
0.7881	Intermediate Similarity	NPD6869	Approved
0.7881	Intermediate Similarity	NPD6847	Approved
0.7881	Intermediate Similarity	NPD8130	Phase 1
0.7874	Intermediate Similarity	NPD7319	Approved
0.7863	Intermediate Similarity	NPD6012	Approved
0.7863	Intermediate Similarity	NPD6013	Approved
0.7863	Intermediate Similarity	NPD6014	Approved
0.7857	Intermediate Similarity	NPD8293	Discontinued
0.7778	Intermediate Similarity	NPD7320	Approved
0.7778	Intermediate Similarity	NPD7507	Approved
0.7778	Intermediate Similarity	NPD6336	Discontinued
0.7692	Intermediate Similarity	NPD6412	Phase 2
0.7692	Intermediate Similarity	NPD5701	Approved
0.7632	Intermediate Similarity	NPD5286	Approved
0.7632	Intermediate Similarity	NPD4696	Approved
0.7632	Intermediate Similarity	NPD5285	Approved
0.7619	Intermediate Similarity	NPD8328	Phase 3
0.7583	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6399	Phase 3
0.7565	Intermediate Similarity	NPD5223	Approved
0.7519	Intermediate Similarity	NPD6033	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.7479	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6079	Approved
0.7456	Intermediate Similarity	NPD4755	Approved
0.744	Intermediate Similarity	NPD7101	Approved
0.744	Intermediate Similarity	NPD7100	Approved
0.7436	Intermediate Similarity	NPD5175	Approved
0.7436	Intermediate Similarity	NPD5174	Approved
0.7434	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6317	Approved
0.7373	Intermediate Similarity	NPD5141	Approved
0.736	Intermediate Similarity	NPD6314	Approved
0.736	Intermediate Similarity	NPD6313	Approved
0.7339	Intermediate Similarity	NPD6274	Approved
0.7333	Intermediate Similarity	NPD4729	Approved
0.7333	Intermediate Similarity	NPD4730	Approved
0.7328	Intermediate Similarity	NPD4700	Approved
0.7323	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7503	Approved
0.7304	Intermediate Similarity	NPD7902	Approved
0.7304	Intermediate Similarity	NPD6084	Phase 2
0.7304	Intermediate Similarity	NPD6083	Phase 2
0.7297	Intermediate Similarity	NPD5328	Approved
0.728	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3573	Approved
0.7257	Intermediate Similarity	NPD4202	Approved
0.7241	Intermediate Similarity	NPD5696	Approved
0.7241	Intermediate Similarity	NPD7638	Approved
0.7222	Intermediate Similarity	NPD7327	Approved
0.7222	Intermediate Similarity	NPD7328	Approved
0.7217	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5221	Approved
0.7217	Intermediate Similarity	NPD5222	Approved
0.7213	Intermediate Similarity	NPD5247	Approved
0.7213	Intermediate Similarity	NPD5249	Phase 3
0.7213	Intermediate Similarity	NPD5248	Approved
0.7213	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5251	Approved
0.7213	Intermediate Similarity	NPD5250	Approved
0.7207	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7748	Approved
0.7188	Intermediate Similarity	NPD8033	Approved
0.7182	Intermediate Similarity	NPD6409	Approved
0.7182	Intermediate Similarity	NPD7521	Approved
0.7182	Intermediate Similarity	NPD7334	Approved
0.7182	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6684	Approved
0.7182	Intermediate Similarity	NPD7146	Approved
0.7182	Intermediate Similarity	NPD5330	Approved
0.7179	Intermediate Similarity	NPD7639	Approved
0.7179	Intermediate Similarity	NPD7640	Approved
0.7168	Intermediate Similarity	NPD5284	Approved
0.7168	Intermediate Similarity	NPD5281	Approved
0.7167	Intermediate Similarity	NPD4768	Approved
0.7167	Intermediate Similarity	NPD4767	Approved
0.7165	Intermediate Similarity	NPD7516	Approved
0.7155	Intermediate Similarity	NPD5173	Approved
0.7143	Intermediate Similarity	NPD4754	Approved
0.7131	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5695	Phase 3
0.7109	Intermediate Similarity	NPD8377	Approved
0.7109	Intermediate Similarity	NPD8294	Approved
0.7073	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5135	Approved
0.7073	Intermediate Similarity	NPD5169	Approved
0.7073	Intermediate Similarity	NPD6371	Approved
0.7069	Intermediate Similarity	NPD4697	Phase 3
0.7063	Intermediate Similarity	NPD6868	Approved
0.7054	Intermediate Similarity	NPD6908	Approved
0.7054	Intermediate Similarity	NPD8379	Approved
0.7054	Intermediate Similarity	NPD8378	Approved
0.7054	Intermediate Similarity	NPD8380	Approved
0.7054	Intermediate Similarity	NPD8335	Approved
0.7054	Intermediate Similarity	NPD6909	Approved
0.7054	Intermediate Similarity	NPD6903	Approved
0.7054	Intermediate Similarity	NPD8296	Approved
0.7049	Intermediate Similarity	NPD6686	Approved
0.7049	Intermediate Similarity	NPD5128	Approved
0.7043	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6001	Approved
0.7043	Intermediate Similarity	NPD7900	Approved
0.7027	Intermediate Similarity	NPD3618	Phase 1
0.7018	Intermediate Similarity	NPD8035	Phase 2
0.7018	Intermediate Similarity	NPD7515	Phase 2
0.7018	Intermediate Similarity	NPD8034	Phase 2
0.7016	Intermediate Similarity	NPD5217	Approved
0.7016	Intermediate Similarity	NPD5216	Approved
0.7016	Intermediate Similarity	NPD5215	Approved
0.7016	Intermediate Similarity	NPD5127	Approved
0.6991	Remote Similarity	NPD6673	Approved
0.6991	Remote Similarity	NPD6080	Approved
0.6991	Remote Similarity	NPD6904	Approved
0.6983	Remote Similarity	NPD4629	Approved
0.6983	Remote Similarity	NPD5210	Approved
0.6967	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7260	Phase 2
0.696	Remote Similarity	NPD6053	Discontinued
0.6949	Remote Similarity	NPD4225	Approved
0.6947	Remote Similarity	NPD6067	Discontinued
0.6923	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD8517	Approved
0.6923	Remote Similarity	NPD6921	Approved
0.6923	Remote Similarity	NPD8515	Approved
0.6906	Remote Similarity	NPD6333	Approved
0.6906	Remote Similarity	NPD6334	Approved
0.6905	Remote Similarity	NPD8133	Approved
0.6903	Remote Similarity	NPD5737	Approved
0.6903	Remote Similarity	NPD6672	Approved
0.6899	Remote Similarity	NPD4522	Approved
0.6889	Remote Similarity	NPD5956	Approved
0.687	Remote Similarity	NPD6411	Approved
0.685	Remote Similarity	NPD5167	Approved
0.6847	Remote Similarity	NPD3133	Approved
0.6847	Remote Similarity	NPD4786	Approved
0.6847	Remote Similarity	NPD3666	Approved
0.6847	Remote Similarity	NPD3665	Phase 1
0.6842	Remote Similarity	NPD4753	Phase 2
0.6829	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4223	Phase 3
0.6818	Remote Similarity	NPD4221	Approved
0.6786	Remote Similarity	NPD5329	Approved
0.6783	Remote Similarity	NPD5785	Approved
0.6783	Remote Similarity	NPD5207	Approved
0.6754	Remote Similarity	NPD5208	Approved
0.6727	Remote Similarity	NPD5369	Approved
0.6726	Remote Similarity	NPD5690	Phase 2
0.6726	Remote Similarity	NPD6098	Approved
0.6724	Remote Similarity	NPD6050	Approved
0.6724	Remote Similarity	NPD5693	Phase 1
0.6724	Remote Similarity	NPD5694	Approved
0.6696	Remote Similarity	NPD4197	Approved
0.6696	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6101	Approved
0.6694	Remote Similarity	NPD1700	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD8170	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