NPASS Compound

Structure

NPC22376 OpenBabel07101718202D 27 30 0 0 1 0 0 0 0 0999 V2000 0.4202 -2.0480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5107 1.1346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4124 0.7962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0336 -0.4785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8065 -2.1071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5893 -1.5266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2717 -1.6505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2046 0.3325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3124 0.2878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5922 -1.1004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2607 -0.9159 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7939 -1.1942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5223 0.4563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0311 -0.6928 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6182 -0.9365 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8309 -1.1942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0506 -0.3943 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6685 0.1845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0915 -0.2782 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5332 -0.2782 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 0.2660 1.3847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2648 -1.9733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0127 -0.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7360 0.4375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7553 0.7931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8744 -1.8649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 20 1 1 0 0 0 12 16 1 0 0 0 0 12 19 1 6 0 0 0 13 21 1 6 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 17 1 0 0 0 0 15 27 1 6 0 0 0 16 20 1 1 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 21 1 0 0 0 0 19 4 1 6 0 0 0 19 25 1 0 0 0 0 20 8 1 1 0 0 0 21 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	917.54
Volume:	933.87
LogP:	3.706
LogD:	4.44
LogS:	-3.851
# Rotatable Bonds:	9
TPSA:	245.94
# H-Bond Aceptor:	18
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.195
Synthetic Accessibility Score:	6.027
Fsp3:	0.667
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:	-6.143
MDCK Permeability:	1.3947731531516183e-05
Pgp-inhibitor:	0.911
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.68
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	73.91120147705078%
Volume Distribution (VD):	0.511
Pgp-substrate:	10.004487991333008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.41
CYP2D6-inhibitor:	0.091
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.05

ADMET: Excretion

Clearance (CL):	3.736
Half-life (T1/2):	0.68

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.996
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.953
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.147
Carcinogencity:	0.18
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.174

Download Data

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

Natural Product: NPC22376

Natural Product ID:	NPC22376
*Common Name:**	Rhodomolin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LVTNTYUMDOSYCN-UNXWYAAGSA-N
Standard InCHI:	InChI=1S/C21H34O6/c1-10-11-6-7-12-16(23)20(11,9-19(12,4)25)8-13(22)21(26)14(10)15(27-5)17(24)18(21,2)3/h11-17,22-26H,1,6-9H2,2-5H3/t11-,12+,13+,14+,15-,16+,17-,19+,20-,21+/m0/s1
SMILES:	C=C1[C@@H]2CC[C@@H]3[C@H]([C@@]2(C[C@H]([C@]2([C@H]1[C@@H]([C@@H](C2(C)C)O)OC)O)O)C[C@@]3(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464146
PubChem CID:	11292000
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	flowers	n.a.	n.a.	PMID[15974620]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[26599832]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29272126]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25980	Rhododendron molle	Species	Ericaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	37.8	ug.mL-1	PMID[517486]

☑ 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 NPC22376 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	217
0.1-0.2	2419
0.2-0.3	9597
0.3-0.4	14549
0.4-0.5	6559
0.5-0.6	6490
0.6-0.7	2652
0.7-0.8	155
0.8-0.85	25
0.85-0.9	11
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC242016
0.9286	High Similarity	NPC145245
0.9205	High Similarity	NPC39453
0.8415	Intermediate Similarity	NPC131584
0.8415	Intermediate Similarity	NPC139765
0.8353	Intermediate Similarity	NPC66766
0.8353	Intermediate Similarity	NPC117137
0.8202	Intermediate Similarity	NPC121981
0.8182	Intermediate Similarity	NPC255882
0.8068	Intermediate Similarity	NPC29342
0.8068	Intermediate Similarity	NPC232023
0.8068	Intermediate Similarity	NPC2572
0.8065	Intermediate Similarity	NPC98193
0.8043	Intermediate Similarity	NPC470832
0.8022	Intermediate Similarity	NPC473436
0.798	Intermediate Similarity	NPC474464
0.7957	Intermediate Similarity	NPC210268
0.7931	Intermediate Similarity	NPC78545
0.7931	Intermediate Similarity	NPC71535
0.79	Intermediate Similarity	NPC474015
0.7879	Intermediate Similarity	NPC475701
0.7865	Intermediate Similarity	NPC260852
0.7865	Intermediate Similarity	NPC211135
0.7865	Intermediate Similarity	NPC85095
0.7865	Intermediate Similarity	NPC216420
0.7802	Intermediate Similarity	NPC64862
0.7789	Intermediate Similarity	NPC473258
0.7778	Intermediate Similarity	NPC256567
0.7732	Intermediate Similarity	NPC76486
0.7708	Intermediate Similarity	NPC30477
0.7708	Intermediate Similarity	NPC473348
0.7701	Intermediate Similarity	NPC477819
0.7701	Intermediate Similarity	NPC477817
0.7674	Intermediate Similarity	NPC293223
0.767	Intermediate Similarity	NPC128133
0.7667	Intermediate Similarity	NPC69953
0.766	Intermediate Similarity	NPC473956
0.766	Intermediate Similarity	NPC475751
0.7653	Intermediate Similarity	NPC275865
0.764	Intermediate Similarity	NPC157655
0.764	Intermediate Similarity	NPC473257
0.7634	Intermediate Similarity	NPC475664
0.7624	Intermediate Similarity	NPC288502
0.7624	Intermediate Similarity	NPC121518
0.7624	Intermediate Similarity	NPC471111
0.7624	Intermediate Similarity	NPC103298
0.7624	Intermediate Similarity	NPC475335
0.7624	Intermediate Similarity	NPC475331
0.7624	Intermediate Similarity	NPC80809
0.7624	Intermediate Similarity	NPC201144
0.7624	Intermediate Similarity	NPC181104
0.7614	Intermediate Similarity	NPC5604
0.7609	Intermediate Similarity	NPC201273
0.7582	Intermediate Similarity	NPC86238
0.7582	Intermediate Similarity	NPC124172
0.7579	Intermediate Similarity	NPC219516
0.7576	Intermediate Similarity	NPC471247
0.7576	Intermediate Similarity	NPC91497
0.7558	Intermediate Similarity	NPC36479
0.7553	Intermediate Similarity	NPC109744
0.7553	Intermediate Similarity	NPC105495
0.7551	Intermediate Similarity	NPC475033
0.7551	Intermediate Similarity	NPC475032
0.7549	Intermediate Similarity	NPC60315
0.7549	Intermediate Similarity	NPC475290
0.7528	Intermediate Similarity	NPC47149
0.7527	Intermediate Similarity	NPC186145
0.7527	Intermediate Similarity	NPC474657
0.7525	Intermediate Similarity	NPC475334
0.7525	Intermediate Similarity	NPC475623
0.7525	Intermediate Similarity	NPC473694
0.75	Intermediate Similarity	NPC31828
0.75	Intermediate Similarity	NPC475
0.75	Intermediate Similarity	NPC144486
0.75	Intermediate Similarity	NPC472502
0.75	Intermediate Similarity	NPC296620
0.75	Intermediate Similarity	NPC470168
0.75	Intermediate Similarity	NPC471112
0.75	Intermediate Similarity	NPC474022
0.75	Intermediate Similarity	NPC26046
0.75	Intermediate Similarity	NPC73385
0.75	Intermediate Similarity	NPC290731
0.7475	Intermediate Similarity	NPC309493
0.7475	Intermediate Similarity	NPC5358
0.7475	Intermediate Similarity	NPC216260
0.7474	Intermediate Similarity	NPC107189
0.7473	Intermediate Similarity	NPC110778
0.7471	Intermediate Similarity	NPC91573
0.7453	Intermediate Similarity	NPC19888
0.7451	Intermediate Similarity	NPC473577
0.7451	Intermediate Similarity	NPC474550
0.7451	Intermediate Similarity	NPC475585
0.7451	Intermediate Similarity	NPC475521
0.7449	Intermediate Similarity	NPC306797
0.7449	Intermediate Similarity	NPC111834
0.7449	Intermediate Similarity	NPC288970
0.7449	Intermediate Similarity	NPC292718
0.7449	Intermediate Similarity	NPC472989
0.7449	Intermediate Similarity	NPC169270
0.7442	Intermediate Similarity	NPC475458
0.7426	Intermediate Similarity	NPC228049
0.7426	Intermediate Similarity	NPC52585
0.7426	Intermediate Similarity	NPC68630
0.7426	Intermediate Similarity	NPC177701
0.7426	Intermediate Similarity	NPC31085
0.7426	Intermediate Similarity	NPC22634
0.7423	Intermediate Similarity	NPC3359
0.7423	Intermediate Similarity	NPC65402
0.7423	Intermediate Similarity	NPC127718
0.7419	Intermediate Similarity	NPC6605
0.7419	Intermediate Similarity	NPC476217
0.7419	Intermediate Similarity	NPC24277
0.7416	Intermediate Similarity	NPC269333
0.7416	Intermediate Similarity	NPC24504
0.7416	Intermediate Similarity	NPC476316
0.74	Intermediate Similarity	NPC471242
0.7396	Intermediate Similarity	NPC41554
0.7396	Intermediate Similarity	NPC97404
0.7391	Intermediate Similarity	NPC475798
0.7391	Intermediate Similarity	NPC127606
0.7386	Intermediate Similarity	NPC185915
0.7379	Intermediate Similarity	NPC26798
0.7374	Intermediate Similarity	NPC261807
0.7374	Intermediate Similarity	NPC274793
0.7368	Intermediate Similarity	NPC74258
0.7368	Intermediate Similarity	NPC470361
0.7363	Intermediate Similarity	NPC7988
0.7363	Intermediate Similarity	NPC470614
0.7363	Intermediate Similarity	NPC475388
0.7363	Intermediate Similarity	NPC1272
0.7363	Intermediate Similarity	NPC30166
0.7358	Intermediate Similarity	NPC197231
0.7356	Intermediate Similarity	NPC3403
0.7356	Intermediate Similarity	NPC317242
0.7353	Intermediate Similarity	NPC471467
0.7347	Intermediate Similarity	NPC241047
0.7347	Intermediate Similarity	NPC8774
0.7347	Intermediate Similarity	NPC292178
0.7347	Intermediate Similarity	NPC86893
0.734	Intermediate Similarity	NPC477600
0.734	Intermediate Similarity	NPC474174
0.734	Intermediate Similarity	NPC189777
0.734	Intermediate Similarity	NPC251808
0.734	Intermediate Similarity	NPC472396
0.7333	Intermediate Similarity	NPC475679
0.7327	Intermediate Similarity	NPC49532
0.7327	Intermediate Similarity	NPC155974
0.7327	Intermediate Similarity	NPC31346
0.7326	Intermediate Similarity	NPC95165
0.732	Intermediate Similarity	NPC470187
0.732	Intermediate Similarity	NPC137461
0.7317	Intermediate Similarity	NPC300442
0.7308	Intermediate Similarity	NPC226642
0.7303	Intermediate Similarity	NPC42853
0.7303	Intermediate Similarity	NPC472501
0.7303	Intermediate Similarity	NPC301707
0.7303	Intermediate Similarity	NPC67657
0.7303	Intermediate Similarity	NPC472500
0.7303	Intermediate Similarity	NPC472499
0.7303	Intermediate Similarity	NPC18857
0.73	Intermediate Similarity	NPC476895
0.73	Intermediate Similarity	NPC469725
0.73	Intermediate Similarity	NPC470067
0.73	Intermediate Similarity	NPC470066
0.7292	Intermediate Similarity	NPC204188
0.7292	Intermediate Similarity	NPC10274
0.7292	Intermediate Similarity	NPC11216
0.7292	Intermediate Similarity	NPC123252
0.7292	Intermediate Similarity	NPC3345
0.7292	Intermediate Similarity	NPC80561
0.7292	Intermediate Similarity	NPC291484
0.7292	Intermediate Similarity	NPC329596
0.7292	Intermediate Similarity	NPC194485
0.7292	Intermediate Similarity	NPC219937
0.7292	Intermediate Similarity	NPC53890
0.7283	Intermediate Similarity	NPC193870
0.7283	Intermediate Similarity	NPC132635
0.7283	Intermediate Similarity	NPC470929
0.7283	Intermediate Similarity	NPC477818
0.7283	Intermediate Similarity	NPC141941
0.7283	Intermediate Similarity	NPC207013
0.7273	Intermediate Similarity	NPC227583
0.7273	Intermediate Similarity	NPC98457
0.7273	Intermediate Similarity	NPC329626
0.7273	Intermediate Similarity	NPC163597
0.7273	Intermediate Similarity	NPC12103
0.7263	Intermediate Similarity	NPC474668
0.7263	Intermediate Similarity	NPC2158
0.7263	Intermediate Similarity	NPC160304
0.7263	Intermediate Similarity	NPC476723
0.7263	Intermediate Similarity	NPC470542
0.7263	Intermediate Similarity	NPC476724
0.7255	Intermediate Similarity	NPC136816
0.7253	Intermediate Similarity	NPC118116
0.7241	Intermediate Similarity	NPC48795
0.7241	Intermediate Similarity	NPC308440
0.7241	Intermediate Similarity	NPC472503
0.7238	Intermediate Similarity	NPC476513
0.7238	Intermediate Similarity	NPC475634
0.7234	Intermediate Similarity	NPC6391

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 NPC22376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	3062
0.2-0.3	4053
0.3-0.4	1230
0.4-0.5	268
0.5-0.6	253
0.6-0.7	58
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7158	Intermediate Similarity	NPD7524	Approved
0.7143	Intermediate Similarity	NPD7525	Registered
0.7021	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6695	Phase 3
0.6889	Remote Similarity	NPD6933	Approved
0.6783	Remote Similarity	NPD8033	Approved
0.6782	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6930	Phase 2
0.6774	Remote Similarity	NPD6931	Approved
0.6703	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6633	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7750	Discontinued
0.663	Remote Similarity	NPD6932	Approved
0.6609	Remote Similarity	NPD7516	Approved
0.6596	Remote Similarity	NPD4748	Discontinued
0.6593	Remote Similarity	NPD7339	Approved
0.6593	Remote Similarity	NPD6942	Approved
0.6552	Remote Similarity	NPD6054	Approved
0.6552	Remote Similarity	NPD8294	Approved
0.6552	Remote Similarity	NPD6059	Approved
0.6552	Remote Similarity	NPD8377	Approved
0.6514	Remote Similarity	NPD6412	Phase 2
0.6496	Remote Similarity	NPD8380	Approved
0.6496	Remote Similarity	NPD8379	Approved
0.6496	Remote Similarity	NPD8378	Approved
0.6496	Remote Similarity	NPD8335	Approved
0.6496	Remote Similarity	NPD8296	Approved
0.6489	Remote Similarity	NPD6683	Phase 2
0.6486	Remote Similarity	NPD4634	Approved
0.6484	Remote Similarity	NPD4785	Approved
0.6484	Remote Similarity	NPD4784	Approved
0.6471	Remote Similarity	NPD8171	Discontinued
0.646	Remote Similarity	NPD4632	Approved
0.6455	Remote Similarity	NPD7320	Approved
0.6452	Remote Similarity	NPD6925	Approved
0.6452	Remote Similarity	NPD5776	Phase 2
0.6444	Remote Similarity	NPD4243	Approved
0.6441	Remote Similarity	NPD6370	Approved
0.6429	Remote Similarity	NPD6893	Approved
0.6421	Remote Similarity	NPD6928	Phase 2
0.6421	Remote Similarity	NPD7509	Discontinued
0.6421	Remote Similarity	NPD7514	Phase 3
0.641	Remote Similarity	NPD6319	Approved
0.6392	Remote Similarity	NPD4788	Approved
0.6383	Remote Similarity	NPD7145	Approved
0.6381	Remote Similarity	NPD4755	Approved
0.6373	Remote Similarity	NPD7087	Discontinued
0.6372	Remote Similarity	NPD6053	Discontinued
0.6364	Remote Similarity	NPD7078	Approved
0.6356	Remote Similarity	NPD7503	Approved
0.6356	Remote Similarity	NPD6015	Approved
0.6356	Remote Similarity	NPD6016	Approved
0.6333	Remote Similarity	NPD7492	Approved
0.6321	Remote Similarity	NPD7638	Approved
0.6316	Remote Similarity	NPD7645	Phase 2
0.6316	Remote Similarity	NPD8133	Approved
0.6311	Remote Similarity	NPD4202	Approved
0.6303	Remote Similarity	NPD5988	Approved
0.6281	Remote Similarity	NPD7507	Approved
0.6281	Remote Similarity	NPD6616	Approved
0.6273	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD7128	Approved
0.6273	Remote Similarity	NPD5739	Approved
0.6273	Remote Similarity	NPD6675	Approved
0.6263	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5286	Approved
0.6262	Remote Similarity	NPD7639	Approved
0.6262	Remote Similarity	NPD5285	Approved
0.6262	Remote Similarity	NPD7640	Approved
0.6262	Remote Similarity	NPD4696	Approved
0.6262	Remote Similarity	NPD4700	Approved
0.625	Remote Similarity	NPD7332	Phase 2
0.623	Remote Similarity	NPD8293	Discontinued
0.6228	Remote Similarity	NPD8297	Approved
0.6222	Remote Similarity	NPD6922	Approved
0.6222	Remote Similarity	NPD6923	Approved
0.6214	Remote Similarity	NPD8035	Phase 2
0.6214	Remote Similarity	NPD8034	Phase 2
0.6204	Remote Similarity	NPD4159	Approved
0.6186	Remote Similarity	NPD6902	Approved
0.6186	Remote Similarity	NPD6898	Phase 1
0.6179	Remote Similarity	NPD7736	Approved
0.6176	Remote Similarity	NPD4753	Phase 2
0.6162	Remote Similarity	NPD4786	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6154	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD4787	Phase 1
0.6154	Remote Similarity	NPD7143	Approved
0.6154	Remote Similarity	NPD7144	Approved
0.6147	Remote Similarity	NPD5211	Phase 2
0.6147	Remote Similarity	NPD5225	Approved
0.6147	Remote Similarity	NPD5226	Approved
0.6147	Remote Similarity	NPD4633	Approved
0.6147	Remote Similarity	NPD5224	Approved
0.6129	Remote Similarity	NPD7319	Approved
0.6126	Remote Similarity	NPD6008	Approved
0.6106	Remote Similarity	NPD6372	Approved
0.6106	Remote Similarity	NPD6373	Approved
0.6091	Remote Similarity	NPD5174	Approved
0.6091	Remote Similarity	NPD5175	Approved
0.6087	Remote Similarity	NPD7152	Approved
0.6087	Remote Similarity	NPD7151	Approved
0.6087	Remote Similarity	NPD7150	Approved
0.6075	Remote Similarity	NPD6084	Phase 2
0.6075	Remote Similarity	NPD6083	Phase 2
0.6071	Remote Similarity	NPD5697	Approved
0.6071	Remote Similarity	NPD5701	Approved
0.6064	Remote Similarity	NPD4190	Phase 3
0.6064	Remote Similarity	NPD5275	Approved
0.6055	Remote Similarity	NPD5223	Approved
0.6055	Remote Similarity	NPD5344	Discontinued
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6371	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6048	Remote Similarity	NPD6033	Approved
0.6036	Remote Similarity	NPD5141	Approved
0.6023	Remote Similarity	NPD371	Approved
0.6019	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD3133	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6650	Approved
0.6	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.6	Remote Similarity	NPD6399	Phase 3
0.5984	Remote Similarity	NPD6067	Discontinued
0.5984	Remote Similarity	NPD7604	Phase 2
0.5982	Remote Similarity	NPD4767	Approved
0.5982	Remote Similarity	NPD4768	Approved
0.598	Remote Similarity	NPD4250	Approved
0.598	Remote Similarity	NPD4251	Approved
0.5979	Remote Similarity	NPD4195	Approved
0.5965	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD6014	Approved
0.5965	Remote Similarity	NPD6012	Approved
0.5962	Remote Similarity	NPD3168	Discontinued
0.596	Remote Similarity	NPD3667	Approved
0.595	Remote Similarity	NPD5983	Phase 2
0.5948	Remote Similarity	NPD6882	Approved
0.5946	Remote Similarity	NPD4754	Approved
0.5929	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4821	Approved
0.5918	Remote Similarity	NPD4820	Approved
0.5918	Remote Similarity	NPD4819	Approved
0.5918	Remote Similarity	NPD4822	Approved
0.5909	Remote Similarity	NPD1700	Approved
0.5905	Remote Similarity	NPD7637	Suspended
0.5905	Remote Similarity	NPD6079	Approved
0.5893	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD4629	Approved
0.5888	Remote Similarity	NPD5210	Approved
0.5888	Remote Similarity	NPD5695	Phase 3
0.5887	Remote Similarity	NPD6336	Discontinued
0.5882	Remote Similarity	NPD4249	Approved
0.5882	Remote Similarity	NPD3618	Phase 1
0.5882	Remote Similarity	NPD7115	Discovery
0.5877	Remote Similarity	NPD5128	Approved
0.5877	Remote Similarity	NPD6011	Approved
0.5877	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD4729	Approved
0.5877	Remote Similarity	NPD4730	Approved
0.5876	Remote Similarity	NPD6118	Approved
0.5876	Remote Similarity	NPD6114	Approved
0.5876	Remote Similarity	NPD6115	Approved
0.5876	Remote Similarity	NPD6697	Approved
0.5876	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD4225	Approved
0.5865	Remote Similarity	NPD6051	Approved
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7632	Discontinued
0.5826	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.58	Remote Similarity	NPD4223	Phase 3
0.58	Remote Similarity	NPD4221	Approved
0.5789	Remote Similarity	NPD1810	Approved
0.5789	Remote Similarity	NPD1811	Approved
0.5785	Remote Similarity	NPD4522	Approved
0.5784	Remote Similarity	NPD5329	Approved
0.5784	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD5251	Approved
0.5776	Remote Similarity	NPD5249	Phase 3
0.5776	Remote Similarity	NPD5248	Approved
0.5776	Remote Similarity	NPD5247	Approved
0.5776	Remote Similarity	NPD5250	Approved
0.5773	Remote Similarity	NPD6116	Phase 1
0.5769	Remote Similarity	NPD6903	Approved
0.5758	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD5362	Discontinued
0.5743	Remote Similarity	NPD5331	Approved
0.5743	Remote Similarity	NPD5332	Approved
0.5741	Remote Similarity	NPD6356	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