NPASS Compound

Structure

NPC474516 OpenBabel07101718292D 29 33 0 0 1 0 0 0 0 0999 V2000 -3.0915 2.8914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4467 -0.0650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2568 -1.3749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6722 1.5730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8763 1.9466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9086 0.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2975 0.9157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0771 1.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4715 1.5910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6619 0.8798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1506 -0.2260 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5579 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2707 1.6090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9486 -0.1270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8556 0.5601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0563 0.5421 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4695 -0.6281 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1015 -0.5745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4611 0.8977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7790 -0.5659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2604 0.9157 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4884 0.3859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0678 0.0668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4442 2.1028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7801 -0.7220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0419 -0.4206 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9023 -1.1091 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 -1.7984 -0.7535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 9 1 0 0 0 0 5 13 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 9 19 1 6 0 0 0 10 16 1 0 0 0 0 10 22 2 0 0 0 0 11 18 1 0 0 0 0 11 23 1 1 0 0 0 12 20 1 6 0 0 0 12 21 1 0 0 0 0 13 21 1 1 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 14 25 1 6 0 0 0 15 19 1 6 0 0 0 15 21 1 0 0 0 0 16 19 1 6 0 0 0 16 26 1 0 0 0 0 17 20 1 1 0 0 0 17 29 1 0 0 0 0 18 27 2 0 0 0 0 18 29 1 0 0 0 0 19 2 1 6 0 0 0 20 3 1 1 0 0 0 20 28 1 0 0 0 0 21 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.18
Volume:	391.402
LogP:	0.436
LogD:	-0.366
LogS:	-4.436
# Rotatable Bonds:	0
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.365
Synthetic Accessibility Score:	6.909
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:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.271
MDCK Permeability:	5.9898669860558584e-05
Pgp-inhibitor:	0.47
Pgp-substrate:	0.908
Human Intestinal Absorption (HIA):	0.144
20% Bioavailability (F20%):	0.076
30% Bioavailability (F30%):	0.852

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.626
Plasma Protein Binding (PPB):	25.428871154785156%
Volume Distribution (VD):	0.361
Pgp-substrate:	58.37318420410156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.723
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	2.864
Half-life (T1/2):	0.297

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.501
Drug-inuced Liver Injury (DILI):	0.523
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.68
Maximum Recommended Daily Dose:	0.723
Skin Sensitization:	0.335
Carcinogencity:	0.044
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC474516

Natural Product ID:	NPC474516
*Common Name:**	Cedronolactone D
IUPAC Name:	n.a.
Synonyms:	Cedronolactone D
Standard InCHIKey:	JQRXDXNJURQDRN-JBAAVECLSA-N
Standard InCHI:	InChI=1S/C21H28O8/c1-8-4-10(22)16(26)19(2)9(8)5-13(24)21-7-28-20(3)12(21)6-11(23)18(27)29-17(20)14(25)15(19)21/h4,9,11-17,23-26H,5-7H2,1-3H3/t9-,11-,12-,13+,14+,15+,16+,17-,19-,20-,21+/m0/s1
SMILES:	O[C@H]1C[C@H]2[C@]3([C@@H](OC1=O)[C@@H]([C@H]1[C@@]2(CO3)[C@H](O)C[C@@H]2[C@]1(C)[C@H](O)C(=O)C=C2C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470546
PubChem CID:	44575518
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] 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
NPO22346	Simaba cedron	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644063]
NPO22346	Simaba cedron	Species	Simaroubaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	38.0	ug.mL-1	PMID[527249]

☑ 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 NPC474516 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	238
0.1-0.2	1355
0.2-0.3	4446
0.3-0.4	7679
0.4-0.5	12769
0.5-0.6	6713
0.6-0.7	5979
0.7-0.8	3235
0.8-0.85	211
0.85-0.9	60
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9528	High Similarity	NPC49451
0.9352	High Similarity	NPC251236
0.9352	High Similarity	NPC328374
0.9352	High Similarity	NPC40632
0.9352	High Similarity	NPC96312
0.9327	High Similarity	NPC3316
0.9327	High Similarity	NPC144854
0.9266	High Similarity	NPC287343
0.9266	High Similarity	NPC97908
0.9266	High Similarity	NPC474654
0.9266	High Similarity	NPC470854
0.9266	High Similarity	NPC122033
0.9259	High Similarity	NPC473798
0.9252	High Similarity	NPC289312
0.9252	High Similarity	NPC11252
0.9238	High Similarity	NPC277017
0.9238	High Similarity	NPC154608
0.9238	High Similarity	NPC293850
0.9238	High Similarity	NPC192813
0.9182	High Similarity	NPC17772
0.9182	High Similarity	NPC204552
0.9182	High Similarity	NPC188667
0.9174	High Similarity	NPC134869
0.9174	High Similarity	NPC152199
0.9174	High Similarity	NPC207217
0.9174	High Similarity	NPC235539
0.9167	High Similarity	NPC7921
0.9167	High Similarity	NPC208998
0.9159	High Similarity	NPC201992
0.9083	High Similarity	NPC474906
0.9083	High Similarity	NPC18547
0.9048	High Similarity	NPC102352
0.9018	High Similarity	NPC112038
0.9009	High Similarity	NPC297179
0.8991	High Similarity	NPC51978
0.8981	High Similarity	NPC171888
0.8981	High Similarity	NPC146945
0.8938	High Similarity	NPC102822
0.8938	High Similarity	NPC477046
0.8929	High Similarity	NPC469488
0.8929	High Similarity	NPC470777
0.8899	High Similarity	NPC472002
0.8889	High Similarity	NPC210005
0.8868	High Similarity	NPC181357
0.8839	High Similarity	NPC251310
0.8829	High Similarity	NPC474734
0.8829	High Similarity	NPC179626
0.8796	High Similarity	NPC141350
0.8774	High Similarity	NPC65523
0.8761	High Similarity	NPC476529
0.8761	High Similarity	NPC475775
0.875	High Similarity	NPC470775
0.875	High Similarity	NPC473590
0.875	High Similarity	NPC176513
0.8739	High Similarity	NPC268238
0.8739	High Similarity	NPC143268
0.8739	High Similarity	NPC323821
0.8739	High Similarity	NPC45218
0.8727	High Similarity	NPC90769
0.8727	High Similarity	NPC302146
0.8727	High Similarity	NPC152117
0.8727	High Similarity	NPC234042
0.8707	High Similarity	NPC24651
0.8696	High Similarity	NPC222688
0.8696	High Similarity	NPC312833
0.8684	High Similarity	NPC109607
0.8684	High Similarity	NPC107338
0.8673	High Similarity	NPC470776
0.8661	High Similarity	NPC16081
0.8661	High Similarity	NPC173686
0.8661	High Similarity	NPC259306
0.8661	High Similarity	NPC470628
0.8661	High Similarity	NPC474046
0.8649	High Similarity	NPC194100
0.8621	High Similarity	NPC67251
0.8621	High Similarity	NPC265557
0.8621	High Similarity	NPC18945
0.8621	High Similarity	NPC105926
0.8621	High Similarity	NPC91693
0.8611	High Similarity	NPC230541
0.8584	High Similarity	NPC309433
0.8571	High Similarity	NPC470919
0.8571	High Similarity	NPC117712
0.8571	High Similarity	NPC472972
0.8571	High Similarity	NPC469877
0.8559	High Similarity	NPC280782
0.8547	High Similarity	NPC476729
0.8547	High Similarity	NPC470922
0.8545	High Similarity	NPC474567
0.8532	High Similarity	NPC94942
0.8487	Intermediate Similarity	NPC188291
0.8482	Intermediate Similarity	NPC198539
0.8468	Intermediate Similarity	NPC469655
0.8468	Intermediate Similarity	NPC469656
0.8468	Intermediate Similarity	NPC188738
0.8468	Intermediate Similarity	NPC474846
0.8455	Intermediate Similarity	NPC472534
0.8455	Intermediate Similarity	NPC143706
0.8455	Intermediate Similarity	NPC310546
0.8448	Intermediate Similarity	NPC470779
0.844	Intermediate Similarity	NPC59530
0.843	Intermediate Similarity	NPC100390
0.843	Intermediate Similarity	NPC254614
0.8426	Intermediate Similarity	NPC475036
0.8421	Intermediate Similarity	NPC473968
0.8378	Intermediate Similarity	NPC5284
0.8378	Intermediate Similarity	NPC5103
0.8378	Intermediate Similarity	NPC253906
0.8362	Intermediate Similarity	NPC109973
0.8349	Intermediate Similarity	NPC477877
0.8333	Intermediate Similarity	NPC266728
0.8333	Intermediate Similarity	NPC49492
0.8333	Intermediate Similarity	NPC275583
0.8333	Intermediate Similarity	NPC474575
0.8319	Intermediate Similarity	NPC962
0.8319	Intermediate Similarity	NPC250109
0.8319	Intermediate Similarity	NPC471204
0.8319	Intermediate Similarity	NPC225049
0.8305	Intermediate Similarity	NPC227397
0.8304	Intermediate Similarity	NPC157476
0.8288	Intermediate Similarity	NPC27814
0.8286	Intermediate Similarity	NPC256227
0.8279	Intermediate Similarity	NPC254146
0.8279	Intermediate Similarity	NPC6274
0.8279	Intermediate Similarity	NPC33378
0.8276	Intermediate Similarity	NPC473636
0.8276	Intermediate Similarity	NPC77689
0.8276	Intermediate Similarity	NPC469380
0.8264	Intermediate Similarity	NPC264192
0.8261	Intermediate Similarity	NPC156252
0.8261	Intermediate Similarity	NPC27999
0.8261	Intermediate Similarity	NPC98249
0.8261	Intermediate Similarity	NPC477116
0.8261	Intermediate Similarity	NPC58662
0.8261	Intermediate Similarity	NPC469684
0.8261	Intermediate Similarity	NPC13713
0.8261	Intermediate Similarity	NPC53396
0.8261	Intermediate Similarity	NPC134430
0.8257	Intermediate Similarity	NPC258532
0.8257	Intermediate Similarity	NPC301787
0.8257	Intermediate Similarity	NPC471293
0.825	Intermediate Similarity	NPC476008
0.8246	Intermediate Similarity	NPC299849
0.8246	Intermediate Similarity	NPC247069
0.8246	Intermediate Similarity	NPC243354
0.8235	Intermediate Similarity	NPC473255
0.823	Intermediate Similarity	NPC269530
0.822	Intermediate Similarity	NPC65858
0.8214	Intermediate Similarity	NPC100908
0.8198	Intermediate Similarity	NPC19412
0.8198	Intermediate Similarity	NPC258323
0.8198	Intermediate Similarity	NPC476479
0.8198	Intermediate Similarity	NPC273155
0.819	Intermediate Similarity	NPC106644
0.819	Intermediate Similarity	NPC472397
0.819	Intermediate Similarity	NPC477437
0.819	Intermediate Similarity	NPC471125
0.819	Intermediate Similarity	NPC284707
0.819	Intermediate Similarity	NPC472758
0.819	Intermediate Similarity	NPC477438
0.819	Intermediate Similarity	NPC171905
0.8182	Intermediate Similarity	NPC222833
0.8174	Intermediate Similarity	NPC213084
0.8174	Intermediate Similarity	NPC190185
0.8174	Intermediate Similarity	NPC478216
0.8173	Intermediate Similarity	NPC477435
0.8173	Intermediate Similarity	NPC477436
0.8167	Intermediate Similarity	NPC477745
0.8165	Intermediate Similarity	NPC264048
0.8165	Intermediate Similarity	NPC61442
0.816	Intermediate Similarity	NPC243014
0.8158	Intermediate Similarity	NPC194273
0.8158	Intermediate Similarity	NPC25909
0.8158	Intermediate Similarity	NPC73300
0.8158	Intermediate Similarity	NPC474271
0.8158	Intermediate Similarity	NPC469463
0.8158	Intermediate Similarity	NPC469454
0.8158	Intermediate Similarity	NPC477266
0.8158	Intermediate Similarity	NPC477126
0.8158	Intermediate Similarity	NPC108721
0.8158	Intermediate Similarity	NPC469496
0.8158	Intermediate Similarity	NPC255017
0.8158	Intermediate Similarity	NPC94509
0.8151	Intermediate Similarity	NPC43252
0.8151	Intermediate Similarity	NPC135038
0.8142	Intermediate Similarity	NPC471243
0.8142	Intermediate Similarity	NPC179798
0.8142	Intermediate Similarity	NPC304180
0.8142	Intermediate Similarity	NPC474229
0.8136	Intermediate Similarity	NPC472401
0.8136	Intermediate Similarity	NPC275675
0.8125	Intermediate Similarity	NPC153239
0.8125	Intermediate Similarity	NPC469370
0.8125	Intermediate Similarity	NPC41405
0.812	Intermediate Similarity	NPC471108
0.812	Intermediate Similarity	NPC475041
0.812	Intermediate Similarity	NPC22628
0.812	Intermediate Similarity	NPC268958
0.812	Intermediate Similarity	NPC473839
0.812	Intermediate Similarity	NPC255081

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 NPC474516 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1640
0.2-0.3	3873
0.3-0.4	2184
0.4-0.5	724
0.5-0.6	246
0.6-0.7	132
0.7-0.8	118
0.8-0.85	25
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8362	Intermediate Similarity	NPD6319	Approved
0.8319	Intermediate Similarity	NPD4632	Approved
0.823	Intermediate Similarity	NPD8297	Approved
0.8182	Intermediate Similarity	NPD7128	Approved
0.8182	Intermediate Similarity	NPD5739	Approved
0.8182	Intermediate Similarity	NPD6675	Approved
0.8182	Intermediate Similarity	NPD6402	Approved
0.8125	Intermediate Similarity	NPD6373	Approved
0.8125	Intermediate Similarity	NPD6372	Approved
0.8108	Intermediate Similarity	NPD5697	Approved
0.8108	Intermediate Similarity	NPD5701	Approved
0.8036	Intermediate Similarity	NPD7320	Approved
0.8036	Intermediate Similarity	NPD6899	Approved
0.8036	Intermediate Similarity	NPD6881	Approved
0.7982	Intermediate Similarity	NPD6649	Approved
0.7982	Intermediate Similarity	NPD6650	Approved
0.7965	Intermediate Similarity	NPD6014	Approved
0.7965	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6013	Approved
0.7965	Intermediate Similarity	NPD6012	Approved
0.7949	Intermediate Similarity	NPD6009	Approved
0.7934	Intermediate Similarity	NPD7492	Approved
0.7913	Intermediate Similarity	NPD6882	Approved
0.7899	Intermediate Similarity	NPD6059	Approved
0.7899	Intermediate Similarity	NPD6054	Approved
0.7895	Intermediate Similarity	NPD6883	Approved
0.7895	Intermediate Similarity	NPD7102	Approved
0.7895	Intermediate Similarity	NPD7290	Approved
0.7876	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD6011	Approved
0.787	Intermediate Similarity	NPD4755	Approved
0.7869	Intermediate Similarity	NPD6616	Approved
0.7857	Intermediate Similarity	NPD6008	Approved
0.7851	Intermediate Similarity	NPD8328	Phase 3
0.7833	Intermediate Similarity	NPD5983	Phase 2
0.7833	Intermediate Similarity	NPD6015	Approved
0.7833	Intermediate Similarity	NPD6016	Approved
0.7826	Intermediate Similarity	NPD6869	Approved
0.7826	Intermediate Similarity	NPD6847	Approved
0.7826	Intermediate Similarity	NPD8130	Phase 1
0.7826	Intermediate Similarity	NPD6617	Approved
0.7805	Intermediate Similarity	NPD8293	Discontinued
0.7805	Intermediate Similarity	NPD7078	Approved
0.7769	Intermediate Similarity	NPD5988	Approved
0.7769	Intermediate Similarity	NPD6370	Approved
0.7742	Intermediate Similarity	NPD7736	Approved
0.7739	Intermediate Similarity	NPD4634	Approved
0.7739	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD5285	Approved
0.7727	Intermediate Similarity	NPD5286	Approved
0.7727	Intermediate Similarity	NPD4700	Approved
0.7727	Intermediate Similarity	NPD4696	Approved
0.7705	Intermediate Similarity	NPD7604	Phase 2
0.7672	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5226	Approved
0.7589	Intermediate Similarity	NPD5211	Phase 2
0.7589	Intermediate Similarity	NPD5225	Approved
0.7589	Intermediate Similarity	NPD4633	Approved
0.7589	Intermediate Similarity	NPD5224	Approved
0.7581	Intermediate Similarity	NPD6336	Discontinued
0.7563	Intermediate Similarity	NPD6274	Approved
0.7545	Intermediate Similarity	NPD6083	Phase 2
0.7545	Intermediate Similarity	NPD6084	Phase 2
0.7544	Intermediate Similarity	NPD4768	Approved
0.7544	Intermediate Similarity	NPD4767	Approved
0.7522	Intermediate Similarity	NPD5175	Approved
0.7522	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD6412	Phase 2
0.7456	Intermediate Similarity	NPD5141	Approved
0.7455	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5222	Approved
0.7455	Intermediate Similarity	NPD5221	Approved
0.7455	Intermediate Similarity	NPD4697	Phase 3
0.744	Intermediate Similarity	NPD7507	Approved
0.7431	Intermediate Similarity	NPD7748	Approved
0.7414	Intermediate Similarity	NPD4730	Approved
0.7414	Intermediate Similarity	NPD6686	Approved
0.7414	Intermediate Similarity	NPD4729	Approved
0.7407	Intermediate Similarity	NPD7515	Phase 2
0.7402	Intermediate Similarity	NPD7319	Approved
0.7387	Intermediate Similarity	NPD5173	Approved
0.7387	Intermediate Similarity	NPD7902	Approved
0.7383	Intermediate Similarity	NPD5328	Approved
0.7377	Intermediate Similarity	NPD7101	Approved
0.7377	Intermediate Similarity	NPD7100	Approved
0.7368	Intermediate Similarity	NPD4754	Approved
0.7364	Intermediate Similarity	NPD5695	Phase 3
0.7355	Intermediate Similarity	NPD7115	Discovery
0.7355	Intermediate Similarity	NPD6317	Approved
0.7339	Intermediate Similarity	NPD6399	Phase 3
0.7323	Intermediate Similarity	NPD6033	Approved
0.7321	Intermediate Similarity	NPD5696	Approved
0.7321	Intermediate Similarity	NPD7638	Approved
0.7321	Intermediate Similarity	NPD4225	Approved
0.7295	Intermediate Similarity	NPD6335	Approved
0.7295	Intermediate Similarity	NPD6313	Approved
0.7295	Intermediate Similarity	NPD6314	Approved
0.7288	Intermediate Similarity	NPD5248	Approved
0.7288	Intermediate Similarity	NPD5249	Phase 3
0.7288	Intermediate Similarity	NPD5247	Approved
0.7288	Intermediate Similarity	NPD5250	Approved
0.7288	Intermediate Similarity	NPD5251	Approved
0.7265	Intermediate Similarity	NPD5128	Approved
0.7264	Intermediate Similarity	NPD3618	Phase 1
0.7258	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6908	Approved
0.7258	Intermediate Similarity	NPD6921	Approved
0.7258	Intermediate Similarity	NPD6909	Approved
0.7257	Intermediate Similarity	NPD7639	Approved
0.7257	Intermediate Similarity	NPD7640	Approved
0.7248	Intermediate Similarity	NPD6079	Approved
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.7196	Intermediate Similarity	NPD3573	Approved
0.7182	Intermediate Similarity	NPD4202	Approved
0.7167	Intermediate Similarity	NPD6053	Discontinued
0.7131	Intermediate Similarity	NPD6868	Approved
0.713	Intermediate Similarity	NPD6672	Approved
0.713	Intermediate Similarity	NPD5737	Approved
0.7117	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7900	Approved
0.7097	Intermediate Similarity	NPD7516	Approved
0.7083	Intermediate Similarity	NPD5216	Approved
0.7083	Intermediate Similarity	NPD5217	Approved
0.7083	Intermediate Similarity	NPD5215	Approved
0.7048	Intermediate Similarity	NPD3667	Approved
0.7016	Intermediate Similarity	NPD7328	Approved
0.7016	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD5135	Approved
0.7	Intermediate Similarity	NPD5169	Approved
0.7	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5282	Discontinued
0.6944	Remote Similarity	NPD6684	Approved
0.6944	Remote Similarity	NPD7334	Approved
0.6944	Remote Similarity	NPD6409	Approved
0.6944	Remote Similarity	NPD7521	Approved
0.6944	Remote Similarity	NPD5330	Approved
0.6944	Remote Similarity	NPD7146	Approved
0.6942	Remote Similarity	NPD5127	Approved
0.6937	Remote Similarity	NPD6411	Approved
0.6916	Remote Similarity	NPD3665	Phase 1
0.6916	Remote Similarity	NPD3666	Approved
0.6916	Remote Similarity	NPD3133	Approved
0.6916	Remote Similarity	NPD4786	Approved
0.6909	Remote Similarity	NPD6673	Approved
0.6909	Remote Similarity	NPD6080	Approved
0.6909	Remote Similarity	NPD6904	Approved
0.6903	Remote Similarity	NPD5210	Approved
0.6903	Remote Similarity	NPD4629	Approved
0.6903	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5344	Discontinued
0.6891	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6067	Discontinued
0.6857	Remote Similarity	NPD4695	Discontinued
0.685	Remote Similarity	NPD8379	Approved
0.685	Remote Similarity	NPD8296	Approved
0.685	Remote Similarity	NPD8516	Approved
0.685	Remote Similarity	NPD8033	Approved
0.685	Remote Similarity	NPD8515	Approved
0.685	Remote Similarity	NPD8378	Approved
0.685	Remote Similarity	NPD8517	Approved
0.685	Remote Similarity	NPD8380	Approved
0.685	Remote Similarity	NPD8513	Phase 3
0.685	Remote Similarity	NPD8335	Approved
0.6847	Remote Similarity	NPD46	Approved
0.6847	Remote Similarity	NPD6698	Approved
0.6833	Remote Similarity	NPD5168	Approved
0.6829	Remote Similarity	NPD8133	Approved
0.6818	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6903	Approved
0.6789	Remote Similarity	NPD5279	Phase 3
0.6786	Remote Similarity	NPD5693	Phase 1
0.6774	Remote Similarity	NPD5167	Approved
0.6772	Remote Similarity	NPD8294	Approved
0.6772	Remote Similarity	NPD8377	Approved
0.6767	Remote Similarity	NPD7260	Phase 2
0.6759	Remote Similarity	NPD4197	Approved
0.6757	Remote Similarity	NPD6101	Approved
0.6757	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5779	Approved
0.6726	Remote Similarity	NPD5778	Approved
0.6721	Remote Similarity	NPD6371	Approved
0.6719	Remote Similarity	NPD7503	Approved
0.6697	Remote Similarity	NPD5329	Approved
0.6696	Remote Similarity	NPD5692	Phase 3
0.6695	Remote Similarity	NPD7632	Discontinued
0.6692	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6001	Approved
0.6637	Remote Similarity	NPD8035	Phase 2
0.6637	Remote Similarity	NPD5694	Approved
0.6637	Remote Similarity	NPD5284	Approved
0.6637	Remote Similarity	NPD5281	Approved
0.6637	Remote Similarity	NPD7983	Approved
0.6637	Remote Similarity	NPD8034	Phase 2

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