NPASS Compound

Structure

NPC22388 OpenBabel07101718322D 37 40 0 0 1 0 0 0 0 0999 V2000 -3.1653 4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8126 3.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 -1.3660 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0522 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8344 3.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 -1.3660 0.0000 C 0 0 0 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 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 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 1.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 18 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 30 1 0 0 0 0 14 29 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 25 1 0 0 0 0 16 26 1 0 0 0 0 17 24 1 0 0 0 0 17 27 1 0 0 0 0 19 32 2 0 0 0 0 19 36 1 0 0 0 0 20 33 2 0 0 0 0 20 37 1 0 0 0 0 21 29 1 0 0 0 0 22 34 2 0 0 0 0 23 11 1 1 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 24 29 1 6 0 0 0 25 31 1 6 0 0 0 26 28 1 0 0 0 0 26 36 1 6 0 0 0 27 31 1 6 0 0 0 27 37 1 0 0 0 0 28 30 1 0 0 0 0 28 31 1 6 0 0 0 29 5 1 6 0 0 0 30 6 1 1 0 0 0 30 35 1 0 0 0 0 31 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	516.35
Volume:	552.702
LogP:	5.254
LogD:	4.389
LogS:	-4.589
# Rotatable Bonds:	9
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.34
Synthetic Accessibility Score:	4.975
Fsp3:	0.839
Lipinski Rule-of-5:	Rejected
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:	-4.726
MDCK Permeability:	3.1067869713297114e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.199
30% Bioavailability (F30%):	0.879

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.981
Plasma Protein Binding (PPB):	84.83076477050781%
Volume Distribution (VD):	0.902
Pgp-substrate:	7.098724842071533%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.592
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	5.533
Half-life (T1/2):	0.808

ADMET: Toxicity

hERG Blockers:	0.196
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.789
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.188
Skin Sensitization:	0.678
Carcinogencity:	0.261
Eye Corrosion:	0.089
Eye Irritation:	0.041
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC22388

Natural Product ID:	NPC22388
*Common Name:**	Nanjiol B
IUPAC Name:	[(8R,9S,10R,12R,13S,14S,16S,17R)-12-acetyloxy-17-[(2S)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-16-yl] acetate
Synonyms:
Standard InCHIKey:	OECOVNJCWDRKDP-FZRPPXKSSA-N
Standard InCHI:	InChI=1S/C31H48O6/c1-18(2)9-8-13-30(6,35)28-26(36-19(3)32)16-25-23-11-10-21-15-22(34)12-14-29(21,5)24(23)17-27(31(25,28)7)37-20(4)33/h15,18,23-28,35H,8-14,16-17H2,1-7H3/t23-,24+,25+,26+,27-,28-,29+,30+,31-/m1/s1
SMILES:	CC(CCC[C@@]([C@H]1[C@@H](OC(=O)C)C[C@@H]2[C@]1(C)[C@H](OC(=O)C)C[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)(O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518223
PubChem CID:	11071356
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols 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
NPO20239	Nephthea bayeri	Species	Nephtheidae	Eukaryota	n.a.	Chinese soft coral	n.a.	PMID[12444699]
NPO20239	Nephthea bayeri	Species	Nephtheidae	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
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	5.0	ug.mL-1	PMID[540286]

☑ 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 NPC22388 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	197
0.1-0.2	1207
0.2-0.3	4548
0.3-0.4	9025
0.4-0.5	12004
0.5-0.6	5359
0.6-0.7	5572
0.7-0.8	4228
0.8-0.85	496
0.85-0.9	59
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9053	High Similarity	NPC111015
0.8932	High Similarity	NPC197428
0.8911	High Similarity	NPC231530
0.8911	High Similarity	NPC278628
0.89	High Similarity	NPC140723
0.8878	High Similarity	NPC119036
0.8857	High Similarity	NPC962
0.8857	High Similarity	NPC52634
0.8824	High Similarity	NPC44063
0.8788	High Similarity	NPC167974
0.8788	High Similarity	NPC154072
0.8776	High Similarity	NPC108078
0.8763	High Similarity	NPC279974
0.875	High Similarity	NPC470375
0.875	High Similarity	NPC470376
0.8738	High Similarity	NPC258323
0.8738	High Similarity	NPC94529
0.8737	High Similarity	NPC471896
0.8725	High Similarity	NPC196528
0.8692	High Similarity	NPC266728
0.8692	High Similarity	NPC49492
0.8687	High Similarity	NPC477854
0.8679	High Similarity	NPC178981
0.8679	High Similarity	NPC194100
0.8679	High Similarity	NPC250109
0.8654	High Similarity	NPC2766
0.8646	High Similarity	NPC154101
0.8641	High Similarity	NPC220974
0.8632	High Similarity	NPC475921
0.8632	High Similarity	NPC474704
0.8627	High Similarity	NPC29705
0.86	High Similarity	NPC218383
0.86	High Similarity	NPC83709
0.86	High Similarity	NPC108371
0.8586	High Similarity	NPC18509
0.8585	High Similarity	NPC71348
0.8585	High Similarity	NPC280782
0.8571	High Similarity	NPC69548
0.8571	High Similarity	NPC6206
0.8571	High Similarity	NPC184848
0.8571	High Similarity	NPC469599
0.8558	High Similarity	NPC472219
0.8558	High Similarity	NPC472218
0.8558	High Similarity	NPC472825
0.8558	High Similarity	NPC472217
0.8542	High Similarity	NPC148414
0.8542	High Similarity	NPC111585
0.8542	High Similarity	NPC175628
0.8529	High Similarity	NPC478057
0.8519	High Similarity	NPC270958
0.8515	High Similarity	NPC477052
0.8515	High Similarity	NPC477051
0.8515	High Similarity	NPC477053
0.8511	High Similarity	NPC195640
0.8505	High Similarity	NPC260665
0.8505	High Similarity	NPC317210
0.8505	High Similarity	NPC202889
0.85	High Similarity	NPC114274
0.85	High Similarity	NPC477813
0.8485	Intermediate Similarity	NPC477853
0.8485	Intermediate Similarity	NPC7124
0.8485	Intermediate Similarity	NPC304899
0.8485	Intermediate Similarity	NPC173272
0.8485	Intermediate Similarity	NPC253115
0.8485	Intermediate Similarity	NPC42042
0.8476	Intermediate Similarity	NPC10064
0.8476	Intermediate Similarity	NPC170221
0.8476	Intermediate Similarity	NPC304495
0.8469	Intermediate Similarity	NPC245972
0.8469	Intermediate Similarity	NPC196485
0.8469	Intermediate Similarity	NPC159410
0.8462	Intermediate Similarity	NPC83744
0.8462	Intermediate Similarity	NPC59530
0.8455	Intermediate Similarity	NPC475041
0.8454	Intermediate Similarity	NPC26888
0.8454	Intermediate Similarity	NPC23434
0.8447	Intermediate Similarity	NPC472227
0.8447	Intermediate Similarity	NPC471293
0.8447	Intermediate Similarity	NPC96268
0.8447	Intermediate Similarity	NPC472228
0.8438	Intermediate Similarity	NPC1015
0.8438	Intermediate Similarity	NPC31985
0.8438	Intermediate Similarity	NPC474889
0.8431	Intermediate Similarity	NPC477054
0.8431	Intermediate Similarity	NPC473928
0.8426	Intermediate Similarity	NPC477580
0.8426	Intermediate Similarity	NPC326542
0.8421	Intermediate Similarity	NPC474684
0.8421	Intermediate Similarity	NPC142361
0.8416	Intermediate Similarity	NPC144956
0.8416	Intermediate Similarity	NPC251680
0.8411	Intermediate Similarity	NPC234042
0.8411	Intermediate Similarity	NPC152117
0.8411	Intermediate Similarity	NPC207251
0.8404	Intermediate Similarity	NPC323765
0.84	Intermediate Similarity	NPC190554
0.84	Intermediate Similarity	NPC320306
0.84	Intermediate Similarity	NPC107243
0.84	Intermediate Similarity	NPC475032
0.84	Intermediate Similarity	NPC57416
0.84	Intermediate Similarity	NPC475033
0.84	Intermediate Similarity	NPC253586
0.8396	Intermediate Similarity	NPC179642
0.8396	Intermediate Similarity	NPC101450
0.8396	Intermediate Similarity	NPC76084
0.8396	Intermediate Similarity	NPC163314
0.8396	Intermediate Similarity	NPC474567
0.8393	Intermediate Similarity	NPC222688
0.8384	Intermediate Similarity	NPC472485
0.8384	Intermediate Similarity	NPC470016
0.8384	Intermediate Similarity	NPC162001
0.8384	Intermediate Similarity	NPC45324
0.8384	Intermediate Similarity	NPC317586
0.8384	Intermediate Similarity	NPC222845
0.8384	Intermediate Similarity	NPC271195
0.8384	Intermediate Similarity	NPC48330
0.8381	Intermediate Similarity	NPC329417
0.8378	Intermediate Similarity	NPC109973
0.8367	Intermediate Similarity	NPC170220
0.8367	Intermediate Similarity	NPC141497
0.8367	Intermediate Similarity	NPC470224
0.8367	Intermediate Similarity	NPC475255
0.8367	Intermediate Similarity	NPC107674
0.8365	Intermediate Similarity	NPC469874
0.8365	Intermediate Similarity	NPC152695
0.8365	Intermediate Similarity	NPC476027
0.8365	Intermediate Similarity	NPC85829
0.8365	Intermediate Similarity	NPC470309
0.8365	Intermediate Similarity	NPC48733
0.8365	Intermediate Similarity	NPC171137
0.8365	Intermediate Similarity	NPC50692
0.8365	Intermediate Similarity	NPC202167
0.8365	Intermediate Similarity	NPC220217
0.8365	Intermediate Similarity	NPC475571
0.8365	Intermediate Similarity	NPC97202
0.8365	Intermediate Similarity	NPC296945
0.8365	Intermediate Similarity	NPC214264
0.8365	Intermediate Similarity	NPC302607
0.8365	Intermediate Similarity	NPC319077
0.8365	Intermediate Similarity	NPC150531
0.8365	Intermediate Similarity	NPC119855
0.8365	Intermediate Similarity	NPC260268
0.8365	Intermediate Similarity	NPC257353
0.8365	Intermediate Similarity	NPC49958
0.8364	Intermediate Similarity	NPC153440
0.8364	Intermediate Similarity	NPC118638
0.8351	Intermediate Similarity	NPC171441
0.835	Intermediate Similarity	NPC36688
0.835	Intermediate Similarity	NPC189588
0.835	Intermediate Similarity	NPC159442
0.835	Intermediate Similarity	NPC10232
0.835	Intermediate Similarity	NPC312900
0.835	Intermediate Similarity	NPC187302
0.835	Intermediate Similarity	NPC112009
0.835	Intermediate Similarity	NPC222153
0.835	Intermediate Similarity	NPC97487
0.835	Intermediate Similarity	NPC196471
0.835	Intermediate Similarity	NPC180204
0.835	Intermediate Similarity	NPC160583
0.8349	Intermediate Similarity	NPC469794
0.8349	Intermediate Similarity	NPC190286
0.8349	Intermediate Similarity	NPC298278
0.8349	Intermediate Similarity	NPC72772
0.8333	Intermediate Similarity	NPC222875
0.8333	Intermediate Similarity	NPC121218
0.8333	Intermediate Similarity	NPC268829
0.8333	Intermediate Similarity	NPC295110
0.8333	Intermediate Similarity	NPC247701
0.8333	Intermediate Similarity	NPC193360
0.8333	Intermediate Similarity	NPC253886
0.8333	Intermediate Similarity	NPC25177
0.8318	Intermediate Similarity	NPC118860
0.8318	Intermediate Similarity	NPC43775
0.8318	Intermediate Similarity	NPC214797
0.8318	Intermediate Similarity	NPC207689
0.8318	Intermediate Similarity	NPC231589
0.8317	Intermediate Similarity	NPC20479
0.8317	Intermediate Similarity	NPC78427
0.8317	Intermediate Similarity	NPC153792
0.8317	Intermediate Similarity	NPC186810
0.8317	Intermediate Similarity	NPC28864
0.8317	Intermediate Similarity	NPC271387
0.8317	Intermediate Similarity	NPC38471
0.8317	Intermediate Similarity	NPC162459
0.8317	Intermediate Similarity	NPC98837
0.8317	Intermediate Similarity	NPC38296
0.8317	Intermediate Similarity	NPC474793
0.8317	Intermediate Similarity	NPC176845
0.8317	Intermediate Similarity	NPC16911
0.8316	Intermediate Similarity	NPC73038
0.8302	Intermediate Similarity	NPC241927
0.8302	Intermediate Similarity	NPC258543
0.8302	Intermediate Similarity	NPC472216
0.8302	Intermediate Similarity	NPC284828
0.8302	Intermediate Similarity	NPC5475
0.8302	Intermediate Similarity	NPC173905
0.83	Intermediate Similarity	NPC200054
0.83	Intermediate Similarity	NPC111684
0.83	Intermediate Similarity	NPC471153
0.83	Intermediate Similarity	NPC29410

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 NPC22388 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1484
0.2-0.3	3883
0.3-0.4	2371
0.4-0.5	705
0.5-0.6	186
0.6-0.7	137
0.7-0.8	117
0.8-0.85	60
0.85-0.9	41
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.91	High Similarity	NPD6675	Approved
0.91	High Similarity	NPD6402	Approved
0.91	High Similarity	NPD7128	Approved
0.91	High Similarity	NPD5739	Approved
0.8922	High Similarity	NPD7320	Approved
0.8922	High Similarity	NPD6881	Approved
0.8922	High Similarity	NPD6899	Approved
0.8835	High Similarity	NPD6372	Approved
0.8835	High Similarity	NPD6373	Approved
0.8824	High Similarity	NPD5697	Approved
0.8824	High Similarity	NPD5701	Approved
0.8776	High Similarity	NPD6084	Phase 2
0.8776	High Similarity	NPD6083	Phase 2
0.875	High Similarity	NPD7102	Approved
0.875	High Similarity	NPD6883	Approved
0.875	High Similarity	NPD7290	Approved
0.8725	High Similarity	NPD6008	Approved
0.8667	High Similarity	NPD6869	Approved
0.8667	High Similarity	NPD6617	Approved
0.8667	High Similarity	NPD6649	Approved
0.8667	High Similarity	NPD6847	Approved
0.8667	High Similarity	NPD8130	Phase 1
0.8667	High Similarity	NPD6650	Approved
0.8654	High Similarity	NPD6013	Approved
0.8654	High Similarity	NPD6012	Approved
0.8654	High Similarity	NPD6014	Approved
0.8586	High Similarity	NPD4755	Approved
0.8585	High Similarity	NPD6882	Approved
0.8585	High Similarity	NPD8297	Approved
0.8571	High Similarity	NPD5695	Phase 3
0.8558	High Similarity	NPD6011	Approved
0.8557	High Similarity	NPD4202	Approved
0.8557	High Similarity	NPD6399	Phase 3
0.8511	High Similarity	NPD7334	Approved
0.8511	High Similarity	NPD7146	Approved
0.8511	High Similarity	NPD6409	Approved
0.8511	High Similarity	NPD7521	Approved
0.8511	High Similarity	NPD5330	Approved
0.8511	High Similarity	NPD6684	Approved
0.8505	High Similarity	NPD4632	Approved
0.85	High Similarity	NPD7638	Approved
0.85	High Similarity	NPD5696	Approved
0.8491	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8416	Intermediate Similarity	NPD5285	Approved
0.8416	Intermediate Similarity	NPD7640	Approved
0.8416	Intermediate Similarity	NPD7639	Approved
0.8416	Intermediate Similarity	NPD4700	Approved
0.8416	Intermediate Similarity	NPD4696	Approved
0.8416	Intermediate Similarity	NPD5286	Approved
0.8384	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD6319	Approved
0.8333	Intermediate Similarity	NPD6903	Approved
0.8333	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD6412	Phase 2
0.8283	Intermediate Similarity	NPD7748	Approved
0.8273	Intermediate Similarity	NPD6009	Approved
0.8252	Intermediate Similarity	NPD5224	Approved
0.8252	Intermediate Similarity	NPD5211	Phase 2
0.8252	Intermediate Similarity	NPD4633	Approved
0.8252	Intermediate Similarity	NPD5225	Approved
0.8252	Intermediate Similarity	NPD5226	Approved
0.8247	Intermediate Similarity	NPD6673	Approved
0.8247	Intermediate Similarity	NPD6904	Approved
0.8247	Intermediate Similarity	NPD5328	Approved
0.8247	Intermediate Similarity	NPD4753	Phase 2
0.8247	Intermediate Similarity	NPD6080	Approved
0.8246	Intermediate Similarity	NPD7492	Approved
0.8218	Intermediate Similarity	NPD7902	Approved
0.8214	Intermediate Similarity	NPD6054	Approved
0.8214	Intermediate Similarity	NPD6059	Approved
0.8182	Intermediate Similarity	NPD6274	Approved
0.8174	Intermediate Similarity	NPD6616	Approved
0.8173	Intermediate Similarity	NPD5175	Approved
0.8173	Intermediate Similarity	NPD5174	Approved
0.8158	Intermediate Similarity	NPD7604	Phase 2
0.8155	Intermediate Similarity	NPD5223	Approved
0.8144	Intermediate Similarity	NPD6672	Approved
0.8144	Intermediate Similarity	NPD5737	Approved
0.8142	Intermediate Similarity	NPD5983	Phase 2
0.8125	Intermediate Similarity	NPD7100	Approved
0.8125	Intermediate Similarity	NPD3618	Phase 1
0.8125	Intermediate Similarity	NPD7101	Approved
0.8105	Intermediate Similarity	NPD3665	Phase 1
0.8105	Intermediate Similarity	NPD3666	Approved
0.8105	Intermediate Similarity	NPD3133	Approved
0.8103	Intermediate Similarity	NPD7078	Approved
0.8103	Intermediate Similarity	NPD8293	Discontinued
0.8095	Intermediate Similarity	NPD5141	Approved
0.8085	Intermediate Similarity	NPD4223	Phase 3
0.8085	Intermediate Similarity	NPD4221	Approved
0.8081	Intermediate Similarity	NPD5281	Approved
0.8081	Intermediate Similarity	NPD5284	Approved
0.8081	Intermediate Similarity	NPD7515	Phase 2
0.8081	Intermediate Similarity	NPD6079	Approved
0.807	Intermediate Similarity	NPD6370	Approved
0.8056	Intermediate Similarity	NPD4634	Approved
0.8036	Intermediate Similarity	NPD6335	Approved
0.8034	Intermediate Similarity	NPD7736	Approved
0.8021	Intermediate Similarity	NPD5329	Approved
0.8019	Intermediate Similarity	NPD4767	Approved
0.8019	Intermediate Similarity	NPD4768	Approved
0.8017	Intermediate Similarity	NPD6336	Discontinued
0.8	Intermediate Similarity	NPD4754	Approved
0.7982	Intermediate Similarity	NPD6015	Approved
0.7982	Intermediate Similarity	NPD6908	Approved
0.7982	Intermediate Similarity	NPD6016	Approved
0.7982	Intermediate Similarity	NPD6909	Approved
0.7959	Intermediate Similarity	NPD5208	Approved
0.7946	Intermediate Similarity	NPD6317	Approved
0.7938	Intermediate Similarity	NPD6098	Approved
0.7921	Intermediate Similarity	NPD7900	Approved
0.7921	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD6001	Approved
0.7917	Intermediate Similarity	NPD4197	Approved
0.7917	Intermediate Similarity	NPD4786	Approved
0.7913	Intermediate Similarity	NPD5988	Approved
0.79	Intermediate Similarity	NPD6050	Approved
0.79	Intermediate Similarity	NPD8035	Phase 2
0.79	Intermediate Similarity	NPD8034	Phase 2
0.79	Intermediate Similarity	NPD5693	Phase 1
0.7876	Intermediate Similarity	NPD6314	Approved
0.7876	Intermediate Similarity	NPD6313	Approved
0.787	Intermediate Similarity	NPD4729	Approved
0.787	Intermediate Similarity	NPD5128	Approved
0.787	Intermediate Similarity	NPD4730	Approved
0.7863	Intermediate Similarity	NPD7507	Approved
0.7843	Intermediate Similarity	NPD4629	Approved
0.7843	Intermediate Similarity	NPD5210	Approved
0.78	Intermediate Similarity	NPD5692	Phase 3
0.7788	Intermediate Similarity	NPD7115	Discovery
0.7767	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD5222	Approved
0.7767	Intermediate Similarity	NPD4697	Phase 3
0.7767	Intermediate Similarity	NPD5221	Approved
0.7755	Intermediate Similarity	NPD4689	Approved
0.7755	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD4690	Approved
0.7755	Intermediate Similarity	NPD5205	Approved
0.7755	Intermediate Similarity	NPD4693	Phase 3
0.7755	Intermediate Similarity	NPD4688	Approved
0.7755	Intermediate Similarity	NPD4138	Approved
0.7748	Intermediate Similarity	NPD6053	Discontinued
0.7736	Intermediate Similarity	NPD7632	Discontinued
0.7727	Intermediate Similarity	NPD5248	Approved
0.7727	Intermediate Similarity	NPD5250	Approved
0.7727	Intermediate Similarity	NPD5251	Approved
0.7727	Intermediate Similarity	NPD5249	Phase 3
0.7727	Intermediate Similarity	NPD5247	Approved
0.7723	Intermediate Similarity	NPD5694	Approved
0.7708	Intermediate Similarity	NPD3667	Approved
0.7692	Intermediate Similarity	NPD5173	Approved
0.7672	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7319	Approved
0.7658	Intermediate Similarity	NPD5217	Approved
0.7658	Intermediate Similarity	NPD5216	Approved
0.7658	Intermediate Similarity	NPD5215	Approved
0.7653	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5207	Approved
0.7583	Intermediate Similarity	NPD6033	Approved
0.7576	Intermediate Similarity	NPD4694	Approved
0.7576	Intermediate Similarity	NPD5690	Phase 2
0.7576	Intermediate Similarity	NPD5280	Approved
0.7568	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5135	Approved
0.7568	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5169	Approved
0.7565	Intermediate Similarity	NPD7328	Approved
0.7565	Intermediate Similarity	NPD7327	Approved
0.7544	Intermediate Similarity	NPD6868	Approved
0.7542	Intermediate Similarity	NPD6067	Discontinued
0.75	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD5127	Approved
0.75	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7449	Intermediate Similarity	NPD4788	Approved
0.7436	Intermediate Similarity	NPD8377	Approved
0.7436	Intermediate Similarity	NPD8294	Approved
0.74	Intermediate Similarity	NPD5279	Phase 3
0.7396	Intermediate Similarity	NPD4195	Approved
0.7387	Intermediate Similarity	NPD6686	Approved
0.7374	Intermediate Similarity	NPD3668	Phase 3
0.7373	Intermediate Similarity	NPD8335	Approved
0.7373	Intermediate Similarity	NPD8378	Approved
0.7373	Intermediate Similarity	NPD7503	Approved
0.7373	Intermediate Similarity	NPD8379	Approved
0.7373	Intermediate Similarity	NPD8033	Approved
0.7373	Intermediate Similarity	NPD8296	Approved
0.7373	Intermediate Similarity	NPD8380	Approved
0.7353	Intermediate Similarity	NPD6051	Approved
0.7339	Intermediate Similarity	NPD6052	Approved
0.7333	Intermediate Similarity	NPD5654	Approved
0.7321	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5167	Approved
0.7297	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6114	Approved
0.7292	Intermediate Similarity	NPD6118	Approved
0.7292	Intermediate Similarity	NPD6115	Approved
0.7292	Intermediate Similarity	NPD6697	Approved
0.725	Intermediate Similarity	NPD8328	Phase 3

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