NPASS Compound

Structure

NPC106228 OpenBabel07101719242D 26 30 0 0 1 0 0 0 0 0999 V2000 3.3544 -3.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9638 0.5980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8634 -3.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9708 -1.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4837 -0.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1555 -2.9666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8095 -0.5257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2535 -2.1383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4381 -0.2115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7990 -0.8055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9056 -2.3591 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5782 -0.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8264 -1.5155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2513 -0.1234 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4176 -1.6557 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4042 -1.5085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6540 -2.4409 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5597 -1.4580 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7501 -0.6074 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0608 0.2252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7894 -1.4495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5565 0.7924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7085 -0.7218 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 -1.5691 -2.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6183 -0.7116 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 12 1 0 0 0 0 5 10 1 0 0 0 0 5 13 1 0 0 0 0 6 11 1 0 0 0 0 6 17 1 0 0 0 0 7 24 1 0 0 0 0 9 2 1 1 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 18 1 1 0 0 0 11 18 1 1 0 0 0 11 25 1 0 0 0 0 12 20 2 0 0 0 0 12 26 1 0 0 0 0 13 21 2 0 0 0 0 13 25 1 0 0 0 0 14 19 1 1 0 0 0 14 22 1 0 0 0 0 15 8 1 6 0 0 0 15 17 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 6 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 3 1 6 0 0 0 18 7 1 6 0 0 0 19 23 1 6 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.15
Volume:	348.02
LogP:	2.373
LogD:	1.281
LogS:	-3.428
# Rotatable Bonds:	1
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	6.583
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.704
MDCK Permeability:	8.715376679901965e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.99
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.83

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.589
Plasma Protein Binding (PPB):	75.43419647216797%
Volume Distribution (VD):	1.309
Pgp-substrate:	28.00070571899414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.252
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.221
CYP3A4-inhibitor:	0.579
CYP3A4-substrate:	0.186

ADMET: Excretion

Clearance (CL):	5.693
Half-life (T1/2):	0.764

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.551
Drug-inuced Liver Injury (DILI):	0.815
AMES Toxicity:	0.224
Rat Oral Acute Toxicity:	0.892
Maximum Recommended Daily Dose:	0.512
Skin Sensitization:	0.197
Carcinogencity:	0.725
Eye Corrosion:	0.005
Eye Irritation:	0.015
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC106228

Natural Product ID:	NPC106228
*Common Name:**	Cedronolactone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QFFKFFIFIWKYEB-HVOPIMCPSA-N
Standard InCHI:	InChI=1S/C19H24O7/c1-8-4-12(20)26-15(8)17(3)6-11-18-7-24-19(23,16(17)18)14(22)9(2)10(18)5-13(21)25-11/h4,9-11,14-16,22-23H,5-7H2,1-3H3/t9-,10+,11-,14-,15-,16-,17-,18-,19+/m1/s1
SMILES:	CC1=CC(=O)O[C@H]1[C@@]1(C)C[C@@H]2[C@@]34CO[C@@]([C@@H]([C@H](C)[C@@H]3CC(=O)O2)O)([C@H]14)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517085
PubChem CID:	10451401
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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	=	6.5	ug.mL-1	PMID[551391]

☑ 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 NPC106228 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	1321
0.2-0.3	4296
0.3-0.4	7800
0.4-0.5	13153
0.5-0.6	6224
0.6-0.7	6640
0.7-0.8	2787
0.8-0.85	217
0.85-0.9	15
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC138372
0.9725	High Similarity	NPC19028
0.9725	High Similarity	NPC9674
0.9358	High Similarity	NPC178289
0.8947	High Similarity	NPC472004
0.8879	High Similarity	NPC27363
0.8729	High Similarity	NPC250556
0.8729	High Similarity	NPC469750
0.8655	High Similarity	NPC240070
0.8655	High Similarity	NPC146456
0.8655	High Similarity	NPC471356
0.8655	High Similarity	NPC117702
0.8655	High Similarity	NPC179412
0.8655	High Similarity	NPC471357
0.8655	High Similarity	NPC469757
0.8655	High Similarity	NPC329784
0.8607	High Similarity	NPC88668
0.8596	High Similarity	NPC196931
0.8595	High Similarity	NPC16569
0.8595	High Similarity	NPC159338
0.8595	High Similarity	NPC253456
0.8583	High Similarity	NPC311534
0.8559	High Similarity	NPC471392
0.8559	High Similarity	NPC469382
0.8534	High Similarity	NPC469380
0.8525	High Similarity	NPC42670
0.8525	High Similarity	NPC19124
0.8525	High Similarity	NPC93416
0.8522	High Similarity	NPC473968
0.8512	High Similarity	NPC471361
0.8512	High Similarity	NPC471360
0.8512	High Similarity	NPC469753
0.8512	High Similarity	NPC276838
0.8512	High Similarity	NPC469754
0.8512	High Similarity	NPC469752
0.8512	High Similarity	NPC471359
0.8512	High Similarity	NPC125077
0.8512	High Similarity	NPC329986
0.8512	High Similarity	NPC469751
0.8512	High Similarity	NPC9499
0.8512	High Similarity	NPC10823
0.8512	High Similarity	NPC284406
0.8512	High Similarity	NPC251866
0.8512	High Similarity	NPC86159
0.8512	High Similarity	NPC70542
0.8512	High Similarity	NPC232785
0.8512	High Similarity	NPC180079
0.8512	High Similarity	NPC140092
0.8512	High Similarity	NPC197707
0.8512	High Similarity	NPC219085
0.8512	High Similarity	NPC471358
0.8512	High Similarity	NPC188234
0.8512	High Similarity	NPC471352
0.8512	High Similarity	NPC17896
0.8512	High Similarity	NPC469755
0.8512	High Similarity	NPC91
0.8512	High Similarity	NPC6108
0.8512	High Similarity	NPC89514
0.8487	Intermediate Similarity	NPC469379
0.8487	Intermediate Similarity	NPC75856
0.8487	Intermediate Similarity	NPC86346
0.8462	Intermediate Similarity	NPC470312
0.8455	Intermediate Similarity	NPC298783
0.8455	Intermediate Similarity	NPC104585
0.8455	Intermediate Similarity	NPC157817
0.8455	Intermediate Similarity	NPC225385
0.8455	Intermediate Similarity	NPC477709
0.8455	Intermediate Similarity	NPC476221
0.8435	Intermediate Similarity	NPC266728
0.8435	Intermediate Similarity	NPC49492
0.8435	Intermediate Similarity	NPC471816
0.843	Intermediate Similarity	NPC473888
0.8403	Intermediate Similarity	NPC473979
0.8393	Intermediate Similarity	NPC143706
0.8393	Intermediate Similarity	NPC472534
0.8387	Intermediate Similarity	NPC471234
0.8376	Intermediate Similarity	NPC475775
0.8376	Intermediate Similarity	NPC476529
0.8376	Intermediate Similarity	NPC475041
0.8362	Intermediate Similarity	NPC152615
0.8362	Intermediate Similarity	NPC284068
0.8361	Intermediate Similarity	NPC470851
0.8349	Intermediate Similarity	NPC295791
0.8348	Intermediate Similarity	NPC31354
0.8348	Intermediate Similarity	NPC84949
0.8348	Intermediate Similarity	NPC471633
0.8348	Intermediate Similarity	NPC69576
0.8348	Intermediate Similarity	NPC326542
0.8347	Intermediate Similarity	NPC287423
0.8333	Intermediate Similarity	NPC207251
0.8333	Intermediate Similarity	NPC126691
0.8319	Intermediate Similarity	NPC472666
0.8319	Intermediate Similarity	NPC179642
0.8306	Intermediate Similarity	NPC142756
0.8306	Intermediate Similarity	NPC116075
0.8306	Intermediate Similarity	NPC247190
0.8306	Intermediate Similarity	NPC146857
0.8306	Intermediate Similarity	NPC32793
0.8306	Intermediate Similarity	NPC469749
0.8305	Intermediate Similarity	NPC474585
0.8305	Intermediate Similarity	NPC109607
0.8305	Intermediate Similarity	NPC143755
0.8305	Intermediate Similarity	NPC107338
0.8291	Intermediate Similarity	NPC475372
0.8279	Intermediate Similarity	NPC470850
0.8276	Intermediate Similarity	NPC72772
0.8276	Intermediate Similarity	NPC99620
0.8276	Intermediate Similarity	NPC5311
0.8276	Intermediate Similarity	NPC310341
0.8276	Intermediate Similarity	NPC469794
0.8276	Intermediate Similarity	NPC193382
0.8276	Intermediate Similarity	NPC199428
0.8273	Intermediate Similarity	NPC472821
0.8273	Intermediate Similarity	NPC474775
0.8261	Intermediate Similarity	NPC51978
0.8261	Intermediate Similarity	NPC9848
0.8261	Intermediate Similarity	NPC250109
0.8261	Intermediate Similarity	NPC194100
0.8261	Intermediate Similarity	NPC962
0.8261	Intermediate Similarity	NPC312017
0.8261	Intermediate Similarity	NPC178981
0.825	Intermediate Similarity	NPC129992
0.8246	Intermediate Similarity	NPC201992
0.824	Intermediate Similarity	NPC329636
0.823	Intermediate Similarity	NPC257853
0.8226	Intermediate Similarity	NPC471855
0.822	Intermediate Similarity	NPC329905
0.822	Intermediate Similarity	NPC312536
0.8214	Intermediate Similarity	NPC472820
0.8211	Intermediate Similarity	NPC104382
0.8211	Intermediate Similarity	NPC472770
0.8211	Intermediate Similarity	NPC175186
0.8211	Intermediate Similarity	NPC231529
0.8205	Intermediate Similarity	NPC157376
0.8205	Intermediate Similarity	NPC84987
0.8205	Intermediate Similarity	NPC99728
0.8205	Intermediate Similarity	NPC50305
0.8205	Intermediate Similarity	NPC473852
0.8205	Intermediate Similarity	NPC471354
0.8205	Intermediate Similarity	NPC244402
0.8205	Intermediate Similarity	NPC243196
0.8205	Intermediate Similarity	NPC93883
0.8205	Intermediate Similarity	NPC471353
0.8205	Intermediate Similarity	NPC471351
0.8205	Intermediate Similarity	NPC290693
0.8205	Intermediate Similarity	NPC309034
0.8205	Intermediate Similarity	NPC34390
0.8205	Intermediate Similarity	NPC142066
0.8205	Intermediate Similarity	NPC470171
0.8205	Intermediate Similarity	NPC13713
0.8205	Intermediate Similarity	NPC218970
0.8205	Intermediate Similarity	NPC473656
0.8205	Intermediate Similarity	NPC87250
0.8205	Intermediate Similarity	NPC158344
0.8205	Intermediate Similarity	NPC471355
0.8205	Intermediate Similarity	NPC203862
0.8205	Intermediate Similarity	NPC27507
0.8205	Intermediate Similarity	NPC196429
0.8205	Intermediate Similarity	NPC77319
0.8205	Intermediate Similarity	NPC474418
0.819	Intermediate Similarity	NPC90472
0.819	Intermediate Similarity	NPC243354
0.819	Intermediate Similarity	NPC471398
0.8175	Intermediate Similarity	NPC194716
0.8174	Intermediate Similarity	NPC289312
0.8174	Intermediate Similarity	NPC11252
0.8174	Intermediate Similarity	NPC302146
0.8174	Intermediate Similarity	NPC470063
0.8167	Intermediate Similarity	NPC222688
0.8167	Intermediate Similarity	NPC269642
0.8167	Intermediate Similarity	NPC28532
0.8158	Intermediate Similarity	NPC42776
0.8158	Intermediate Similarity	NPC206595
0.8151	Intermediate Similarity	NPC151616
0.8151	Intermediate Similarity	NPC475136
0.8151	Intermediate Similarity	NPC79579
0.8151	Intermediate Similarity	NPC4548
0.8151	Intermediate Similarity	NPC109973
0.8151	Intermediate Similarity	NPC474466
0.8145	Intermediate Similarity	NPC173347
0.8145	Intermediate Similarity	NPC471170
0.8142	Intermediate Similarity	NPC88701
0.8142	Intermediate Similarity	NPC19412
0.8136	Intermediate Similarity	NPC153440
0.8136	Intermediate Similarity	NPC83287
0.8125	Intermediate Similarity	NPC85670
0.8125	Intermediate Similarity	NPC186668
0.8125	Intermediate Similarity	NPC472818
0.812	Intermediate Similarity	NPC190286
0.8115	Intermediate Similarity	NPC47113
0.8115	Intermediate Similarity	NPC174367
0.811	Intermediate Similarity	NPC329675
0.811	Intermediate Similarity	NPC59288
0.8103	Intermediate Similarity	NPC194273
0.8103	Intermediate Similarity	NPC317210
0.8091	Intermediate Similarity	NPC471412
0.8087	Intermediate Similarity	NPC469656
0.8087	Intermediate Similarity	NPC474846
0.8087	Intermediate Similarity	NPC469655
0.8087	Intermediate Similarity	NPC474750

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 NPC106228 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	1614
0.2-0.3	3819
0.3-0.4	2311
0.4-0.5	682
0.5-0.6	256
0.6-0.7	161
0.7-0.8	90
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8729	High Similarity	NPD7507	Approved
0.8512	High Similarity	NPD7319	Approved
0.822	Intermediate Similarity	NPD7516	Approved
0.8136	Intermediate Similarity	NPD7328	Approved
0.8136	Intermediate Similarity	NPD7327	Approved
0.8	Intermediate Similarity	NPD8377	Approved
0.8	Intermediate Similarity	NPD8294	Approved
0.7982	Intermediate Similarity	NPD6686	Approved
0.7934	Intermediate Similarity	NPD8335	Approved
0.7934	Intermediate Similarity	NPD8378	Approved
0.7934	Intermediate Similarity	NPD8380	Approved
0.7934	Intermediate Similarity	NPD8033	Approved
0.7934	Intermediate Similarity	NPD8379	Approved
0.7934	Intermediate Similarity	NPD8296	Approved
0.7909	Intermediate Similarity	NPD7638	Approved
0.7903	Intermediate Similarity	NPD7078	Approved
0.7886	Intermediate Similarity	NPD7492	Approved
0.7851	Intermediate Similarity	NPD6059	Approved
0.7851	Intermediate Similarity	NPD6054	Approved
0.7838	Intermediate Similarity	NPD7640	Approved
0.7838	Intermediate Similarity	NPD7639	Approved
0.7823	Intermediate Similarity	NPD6616	Approved
0.7797	Intermediate Similarity	NPD4632	Approved
0.7787	Intermediate Similarity	NPD6016	Approved
0.7787	Intermediate Similarity	NPD6015	Approved
0.776	Intermediate Similarity	NPD8293	Discontinued
0.7759	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6009	Approved
0.7739	Intermediate Similarity	NPD6412	Phase 2
0.7724	Intermediate Similarity	NPD5988	Approved
0.7724	Intermediate Similarity	NPD6370	Approved
0.7705	Intermediate Similarity	NPD6319	Approved
0.7698	Intermediate Similarity	NPD7736	Approved
0.7672	Intermediate Similarity	NPD7320	Approved
0.7652	Intermediate Similarity	NPD7128	Approved
0.7652	Intermediate Similarity	NPD6008	Approved
0.7652	Intermediate Similarity	NPD6675	Approved
0.7652	Intermediate Similarity	NPD5739	Approved
0.7652	Intermediate Similarity	NPD6402	Approved
0.7586	Intermediate Similarity	NPD5697	Approved
0.7586	Intermediate Similarity	NPD5701	Approved
0.7563	Intermediate Similarity	NPD6053	Discontinued
0.7563	Intermediate Similarity	NPD6882	Approved
0.7563	Intermediate Similarity	NPD8297	Approved
0.7521	Intermediate Similarity	NPD6899	Approved
0.7521	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD7503	Approved
0.7458	Intermediate Similarity	NPD6373	Approved
0.7458	Intermediate Similarity	NPD6372	Approved
0.7458	Intermediate Similarity	NPD6014	Approved
0.7458	Intermediate Similarity	NPD6012	Approved
0.7458	Intermediate Similarity	NPD6013	Approved
0.7434	Intermediate Similarity	NPD4225	Approved
0.7395	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6883	Approved
0.7395	Intermediate Similarity	NPD7102	Approved
0.7395	Intermediate Similarity	NPD7290	Approved
0.7373	Intermediate Similarity	NPD6011	Approved
0.736	Intermediate Similarity	NPD5983	Phase 2
0.7355	Intermediate Similarity	NPD8133	Approved
0.7345	Intermediate Similarity	NPD4755	Approved
0.7333	Intermediate Similarity	NPD6869	Approved
0.7333	Intermediate Similarity	NPD8130	Phase 1
0.7333	Intermediate Similarity	NPD6617	Approved
0.7333	Intermediate Similarity	NPD6649	Approved
0.7333	Intermediate Similarity	NPD6847	Approved
0.7333	Intermediate Similarity	NPD6650	Approved
0.7317	Intermediate Similarity	NPD7115	Discovery
0.7287	Intermediate Similarity	NPD6033	Approved
0.725	Intermediate Similarity	NPD4634	Approved
0.7244	Intermediate Similarity	NPD7604	Phase 2
0.7241	Intermediate Similarity	NPD5211	Phase 2
0.7241	Intermediate Similarity	NPD7632	Discontinued
0.7227	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5286	Approved
0.7217	Intermediate Similarity	NPD5285	Approved
0.7217	Intermediate Similarity	NPD4700	Approved
0.7217	Intermediate Similarity	NPD4696	Approved
0.719	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD6336	Discontinued
0.7119	Intermediate Similarity	NPD5141	Approved
0.7117	Intermediate Similarity	NPD6698	Approved
0.7117	Intermediate Similarity	NPD46	Approved
0.7109	Intermediate Similarity	NPD8328	Phase 3
0.7109	Intermediate Similarity	NPD6067	Discontinued
0.7097	Intermediate Similarity	NPD6274	Approved
0.7094	Intermediate Similarity	NPD4633	Approved
0.7094	Intermediate Similarity	NPD5225	Approved
0.7094	Intermediate Similarity	NPD5226	Approved
0.7094	Intermediate Similarity	NPD5224	Approved
0.7043	Intermediate Similarity	NPD6083	Phase 2
0.7043	Intermediate Similarity	NPD6084	Phase 2
0.7034	Intermediate Similarity	NPD5175	Approved
0.7034	Intermediate Similarity	NPD5174	Approved
0.7027	Intermediate Similarity	NPD5328	Approved
0.7025	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5695	Phase 3
0.7009	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4202	Approved
0.6967	Remote Similarity	NPD6371	Approved
0.6953	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD8516	Approved
0.6953	Remote Similarity	NPD8513	Phase 3
0.6953	Remote Similarity	NPD8515	Approved
0.6953	Remote Similarity	NPD8517	Approved
0.6929	Remote Similarity	NPD7101	Approved
0.6929	Remote Similarity	NPD7100	Approved
0.6917	Remote Similarity	NPD4767	Approved
0.6917	Remote Similarity	NPD4768	Approved
0.6905	Remote Similarity	NPD6317	Approved
0.6903	Remote Similarity	NPD6079	Approved
0.6891	Remote Similarity	NPD4754	Approved
0.687	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5344	Discontinued
0.6852	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6313	Approved
0.685	Remote Similarity	NPD6314	Approved
0.685	Remote Similarity	NPD6335	Approved
0.6842	Remote Similarity	NPD6399	Phase 3
0.6838	Remote Similarity	NPD5696	Approved
0.6833	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6909	Approved
0.6822	Remote Similarity	NPD6908	Approved
0.681	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5222	Approved
0.681	Remote Similarity	NPD4697	Phase 3
0.681	Remote Similarity	NPD5221	Approved
0.6803	Remote Similarity	NPD4729	Approved
0.6803	Remote Similarity	NPD4730	Approved
0.6803	Remote Similarity	NPD5128	Approved
0.6786	Remote Similarity	NPD6903	Approved
0.6783	Remote Similarity	NPD7625	Phase 1
0.6772	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7521	Approved
0.6757	Remote Similarity	NPD5330	Approved
0.6757	Remote Similarity	NPD7146	Approved
0.6757	Remote Similarity	NPD7334	Approved
0.6757	Remote Similarity	NPD6409	Approved
0.6757	Remote Similarity	NPD3618	Phase 1
0.6757	Remote Similarity	NPD6684	Approved
0.6754	Remote Similarity	NPD5693	Phase 1
0.6752	Remote Similarity	NPD5173	Approved
0.6727	Remote Similarity	NPD3133	Approved
0.6727	Remote Similarity	NPD3665	Phase 1
0.6727	Remote Similarity	NPD3666	Approved
0.6726	Remote Similarity	NPD4753	Phase 2
0.6724	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD1700	Approved
0.6694	Remote Similarity	NPD5251	Approved
0.6694	Remote Similarity	NPD5248	Approved
0.6694	Remote Similarity	NPD5249	Phase 3
0.6694	Remote Similarity	NPD5247	Approved
0.6694	Remote Similarity	NPD5250	Approved
0.6692	Remote Similarity	NPD8074	Phase 3
0.6667	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.664	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5217	Approved
0.664	Remote Similarity	NPD5216	Approved
0.664	Remote Similarity	NPD5215	Approved
0.6638	Remote Similarity	NPD6001	Approved
0.6638	Remote Similarity	NPD7748	Approved
0.6637	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7260	Phase 2
0.661	Remote Similarity	NPD7902	Approved
0.6609	Remote Similarity	NPD8035	Phase 2
0.6609	Remote Similarity	NPD8034	Phase 2
0.6609	Remote Similarity	NPD5281	Approved
0.6609	Remote Similarity	NPD7515	Phase 2
0.6609	Remote Similarity	NPD5284	Approved
0.6607	Remote Similarity	NPD4249	Approved
0.6571	Remote Similarity	NPD6333	Approved
0.6571	Remote Similarity	NPD6334	Approved
0.6569	Remote Similarity	NPD6845	Suspended
0.6565	Remote Similarity	NPD6921	Approved
0.6562	Remote Similarity	NPD6868	Approved
0.656	Remote Similarity	NPD5169	Approved
0.656	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.656	Remote Similarity	NPD5135	Approved
0.6552	Remote Similarity	NPD5778	Approved
0.6552	Remote Similarity	NPD5779	Approved
0.6549	Remote Similarity	NPD4250	Approved
0.6549	Remote Similarity	NPD4251	Approved
0.6545	Remote Similarity	NPD6435	Approved
0.6522	Remote Similarity	NPD5785	Approved
0.6522	Remote Similarity	NPD5207	Approved
0.6518	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD5127	Approved
0.65	Remote Similarity	NPD6648	Approved
0.6491	Remote Similarity	NPD6672	Approved
0.6491	Remote Similarity	NPD5737	Approved
0.6486	Remote Similarity	NPD5362	Discontinued
0.6466	Remote Similarity	NPD6411	Approved
0.6466	Remote Similarity	NPD7637	Suspended
0.6466	Remote Similarity	NPD7983	Approved
0.6441	Remote Similarity	NPD4629	Approved
0.6441	Remote Similarity	NPD5210	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