NPASS Compound

Structure

CID39453 OpenBabel06191715372D 29 32 0 0 1 0 0 0 0 0999 V2000 -1.0267 2.1890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9562 0.8027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6978 -0.5210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9235 -0.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4079 -0.5650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4192 1.6048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3328 1.6048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4831 -0.7145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8761 -0.3965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0266 1.2870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1726 1.2050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8496 0.8905 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9024 0.8906 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5695 -0.7143 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2034 0.8907 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5808 1.3593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2689 0.7583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8264 0.7593 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9099 -0.0818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6992 -0.0001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0528 -0.0002 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 -1.6923 1.9822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1781 -1.5270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6616 2.2577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1483 0.9592 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4898 0.3808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7424 -0.5123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6282 1.1709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 11 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 20 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 15 1 0 0 0 0 11 23 2 0 0 0 0 11 29 1 0 0 0 0 12 21 1 1 0 0 0 13 18 1 0 0 0 0 13 20 1 6 0 0 0 14 22 1 6 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 22 1 6 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 19 1 0 0 0 0 17 26 1 6 0 0 0 18 21 1 1 0 0 0 18 29 1 0 0 0 0 19 22 1 0 0 0 0 20 5 1 6 0 0 0 20 27 1 0 0 0 0 21 8 1 1 0 0 0 22 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.23
Volume:	411.101
LogP:	0.896
LogD:	0.512
LogS:	-3.267
# Rotatable Bonds:	2
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	6.463
Fsp3:	0.864
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.864
MDCK Permeability:	2.1628944523399696e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.798
20% Bioavailability (F20%):	0.747
30% Bioavailability (F30%):	0.851

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078
Plasma Protein Binding (PPB):	47.786102294921875%
Volume Distribution (VD):	0.74
Pgp-substrate:	51.30882263183594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.415
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.098
CYP3A4-inhibitor:	0.309
CYP3A4-substrate:	0.098

ADMET: Excretion

Clearance (CL):	1.65
Half-life (T1/2):	0.687

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.364
Drug-inuced Liver Injury (DILI):	0.177
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.563
Skin Sensitization:	0.114
Carcinogencity:	0.037
Eye Corrosion:	0.006
Eye Irritation:	0.037
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC39453

Natural Product ID:	NPC39453
*Common Name:**	Rhodomolin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZVWWJWGGVAZKLX-ZDFGDWHJSA-N
Standard InCHI:	InChI=1S/C22H34O7/c1-10-12-6-7-13-18(29-11(2)23)21(12,9-20(13,5)27)8-14(24)22(28)15(10)16(25)17(26)19(22,3)4/h12-18,24-28H,1,6-9H2,2-5H3/t12-,13+,14+,15+,16-,17-,18+,20+,21-,22+/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)O)O)O)C[C@@]3(C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464147
PubChem CID:	11269868
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	=	25.6	ug.mL-1	PMID[479362]

☑ 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 NPC39453 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	221
0.1-0.2	2047
0.2-0.3	7635
0.3-0.4	15306
0.4-0.5	6013
0.5-0.6	7026
0.6-0.7	4054
0.7-0.8	338
0.8-0.85	22
0.85-0.9	20
0.9-0.95	8
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9205	High Similarity	NPC22376
0.8966	High Similarity	NPC242016
0.8851	High Similarity	NPC29342
0.8851	High Similarity	NPC2572
0.8764	High Similarity	NPC145245
0.8427	Intermediate Similarity	NPC69953
0.8352	Intermediate Similarity	NPC64862
0.8298	Intermediate Similarity	NPC219516
0.8211	Intermediate Similarity	NPC26046
0.8125	Intermediate Similarity	NPC3359
0.8119	Intermediate Similarity	NPC103298
0.8119	Intermediate Similarity	NPC121518
0.8119	Intermediate Similarity	NPC181104
0.8119	Intermediate Similarity	NPC475335
0.8119	Intermediate Similarity	NPC201144
0.8119	Intermediate Similarity	NPC475331
0.8119	Intermediate Similarity	NPC80809
0.8119	Intermediate Similarity	NPC288502
0.809	Intermediate Similarity	NPC117137
0.809	Intermediate Similarity	NPC66766
0.8061	Intermediate Similarity	NPC475033
0.8061	Intermediate Similarity	NPC475032
0.8039	Intermediate Similarity	NPC60315
0.8039	Intermediate Similarity	NPC475290
0.802	Intermediate Similarity	NPC473694
0.802	Intermediate Similarity	NPC475623
0.802	Intermediate Similarity	NPC475334
0.8	Intermediate Similarity	NPC123252
0.8	Intermediate Similarity	NPC53890
0.8	Intermediate Similarity	NPC144486
0.8	Intermediate Similarity	NPC194485
0.8	Intermediate Similarity	NPC10274
0.8	Intermediate Similarity	NPC219937
0.7979	Intermediate Similarity	NPC160304
0.7959	Intermediate Similarity	NPC169270
0.7959	Intermediate Similarity	NPC306797
0.7959	Intermediate Similarity	NPC111834
0.7959	Intermediate Similarity	NPC292718
0.7941	Intermediate Similarity	NPC473577
0.7941	Intermediate Similarity	NPC474550
0.7941	Intermediate Similarity	NPC475585
0.7935	Intermediate Similarity	NPC299963
0.7931	Intermediate Similarity	NPC139765
0.7931	Intermediate Similarity	NPC131584
0.7921	Intermediate Similarity	NPC177701
0.7921	Intermediate Similarity	NPC31085
0.7917	Intermediate Similarity	NPC130840
0.79	Intermediate Similarity	NPC208358
0.79	Intermediate Similarity	NPC108371
0.7879	Intermediate Similarity	NPC274793
0.7872	Intermediate Similarity	NPC5943
0.7864	Intermediate Similarity	NPC119855
0.7864	Intermediate Similarity	NPC220217
0.7857	Intermediate Similarity	NPC292178
0.7857	Intermediate Similarity	NPC86893
0.7857	Intermediate Similarity	NPC241047
0.7843	Intermediate Similarity	NPC471467
0.7835	Intermediate Similarity	NPC470187
0.7822	Intermediate Similarity	NPC49532
0.7822	Intermediate Similarity	NPC155974
0.7802	Intermediate Similarity	NPC118116
0.78	Intermediate Similarity	NPC469725
0.78	Intermediate Similarity	NPC470067
0.78	Intermediate Similarity	NPC470066
0.7789	Intermediate Similarity	NPC476723
0.7789	Intermediate Similarity	NPC476724
0.7778	Intermediate Similarity	NPC299654
0.7778	Intermediate Similarity	NPC304899
0.7778	Intermediate Similarity	NPC471903
0.7778	Intermediate Similarity	NPC253115
0.7767	Intermediate Similarity	NPC474464
0.7766	Intermediate Similarity	NPC475684
0.7766	Intermediate Similarity	NPC131365
0.7766	Intermediate Similarity	NPC121981
0.7742	Intermediate Similarity	NPC255882
0.7736	Intermediate Similarity	NPC6206
0.7732	Intermediate Similarity	NPC249034
0.7717	Intermediate Similarity	NPC472504
0.77	Intermediate Similarity	NPC254121
0.77	Intermediate Similarity	NPC253586
0.7692	Intermediate Similarity	NPC474714
0.7692	Intermediate Similarity	NPC186668
0.7692	Intermediate Similarity	NPC474015
0.7684	Intermediate Similarity	NPC44538
0.7677	Intermediate Similarity	NPC472873
0.767	Intermediate Similarity	NPC475701
0.767	Intermediate Similarity	NPC472821
0.766	Intermediate Similarity	NPC196911
0.766	Intermediate Similarity	NPC266651
0.766	Intermediate Similarity	NPC471379
0.7653	Intermediate Similarity	NPC98193
0.7647	Intermediate Similarity	NPC475617
0.7642	Intermediate Similarity	NPC10064
0.7642	Intermediate Similarity	NPC473570
0.7642	Intermediate Similarity	NPC170221
0.7634	Intermediate Similarity	NPC239308
0.7634	Intermediate Similarity	NPC232023
0.7629	Intermediate Similarity	NPC470832
0.7629	Intermediate Similarity	NPC209816
0.7624	Intermediate Similarity	NPC470068
0.7619	Intermediate Similarity	NPC475781
0.7619	Intermediate Similarity	NPC470169
0.7619	Intermediate Similarity	NPC470170
0.7615	Intermediate Similarity	NPC300051
0.7604	Intermediate Similarity	NPC250687
0.7604	Intermediate Similarity	NPC473436
0.7604	Intermediate Similarity	NPC254572
0.7604	Intermediate Similarity	NPC470260
0.7604	Intermediate Similarity	NPC229407
0.7604	Intermediate Similarity	NPC92370
0.7604	Intermediate Similarity	NPC48824
0.7604	Intermediate Similarity	NPC75443
0.76	Intermediate Similarity	NPC475304
0.7596	Intermediate Similarity	NPC31430
0.7596	Intermediate Similarity	NPC85593
0.7579	Intermediate Similarity	NPC477668
0.7573	Intermediate Similarity	NPC470972
0.7553	Intermediate Similarity	NPC222634
0.7551	Intermediate Similarity	NPC471747
0.7551	Intermediate Similarity	NPC472468
0.7551	Intermediate Similarity	NPC210268
0.7551	Intermediate Similarity	NPC473066
0.7549	Intermediate Similarity	NPC475877
0.7526	Intermediate Similarity	NPC291875
0.7526	Intermediate Similarity	NPC161560
0.7526	Intermediate Similarity	NPC269267
0.7525	Intermediate Similarity	NPC76486
0.7524	Intermediate Similarity	NPC470980
0.75	Intermediate Similarity	NPC196471
0.75	Intermediate Similarity	NPC71535
0.75	Intermediate Similarity	NPC160583
0.75	Intermediate Similarity	NPC474775
0.75	Intermediate Similarity	NPC97487
0.75	Intermediate Similarity	NPC206735
0.75	Intermediate Similarity	NPC30477
0.75	Intermediate Similarity	NPC473348
0.75	Intermediate Similarity	NPC205173
0.75	Intermediate Similarity	NPC474124
0.75	Intermediate Similarity	NPC10232
0.75	Intermediate Similarity	NPC78545
0.75	Intermediate Similarity	NPC187302
0.75	Intermediate Similarity	NPC189588
0.7477	Intermediate Similarity	NPC128133
0.7476	Intermediate Similarity	NPC470054
0.7476	Intermediate Similarity	NPC222875
0.7476	Intermediate Similarity	NPC268829
0.7476	Intermediate Similarity	NPC247701
0.7476	Intermediate Similarity	NPC295110
0.7476	Intermediate Similarity	NPC474022
0.7476	Intermediate Similarity	NPC25177
0.7474	Intermediate Similarity	NPC476725
0.7473	Intermediate Similarity	NPC471045
0.7455	Intermediate Similarity	NPC216665
0.7453	Intermediate Similarity	NPC59530
0.7453	Intermediate Similarity	NPC470166
0.7451	Intermediate Similarity	NPC102426
0.7451	Intermediate Similarity	NPC275865
0.7451	Intermediate Similarity	NPC300179
0.7449	Intermediate Similarity	NPC472466
0.7449	Intermediate Similarity	NPC471378
0.7449	Intermediate Similarity	NPC473269
0.7449	Intermediate Similarity	NPC312471
0.7447	Intermediate Similarity	NPC5958
0.7447	Intermediate Similarity	NPC260852
0.7447	Intermediate Similarity	NPC85095
0.7447	Intermediate Similarity	NPC216420
0.7447	Intermediate Similarity	NPC111409
0.7447	Intermediate Similarity	NPC211135
0.7431	Intermediate Similarity	NPC126691
0.7429	Intermediate Similarity	NPC470061
0.7429	Intermediate Similarity	NPC470064
0.7429	Intermediate Similarity	NPC471111
0.7429	Intermediate Similarity	NPC470058
0.7429	Intermediate Similarity	NPC470060
0.7429	Intermediate Similarity	NPC470043
0.7429	Intermediate Similarity	NPC152966
0.7429	Intermediate Similarity	NPC470057
0.7429	Intermediate Similarity	NPC470062
0.7429	Intermediate Similarity	NPC473543
0.7429	Intermediate Similarity	NPC470059
0.7423	Intermediate Similarity	NPC255176
0.7419	Intermediate Similarity	NPC77003
0.7404	Intermediate Similarity	NPC228049
0.7404	Intermediate Similarity	NPC475344
0.7404	Intermediate Similarity	NPC470053
0.7404	Intermediate Similarity	NPC52585
0.7404	Intermediate Similarity	NPC68630
0.7404	Intermediate Similarity	NPC214714
0.7404	Intermediate Similarity	NPC22388
0.7404	Intermediate Similarity	NPC200672
0.7404	Intermediate Similarity	NPC165578
0.7404	Intermediate Similarity	NPC476471
0.74	Intermediate Similarity	NPC473258
0.74	Intermediate Similarity	NPC474922
0.74	Intermediate Similarity	NPC470424
0.74	Intermediate Similarity	NPC277399
0.74	Intermediate Similarity	NPC472467
0.7396	Intermediate Similarity	NPC215968
0.7396	Intermediate Similarity	NPC80590
0.7396	Intermediate Similarity	NPC155531

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 NPC39453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	2662
0.2-0.3	4103
0.3-0.4	1475
0.4-0.5	318
0.5-0.6	269
0.6-0.7	110
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
0.7217	Intermediate Similarity	NPD8033	Approved
0.7105	Intermediate Similarity	NPD7328	Approved
0.7105	Intermediate Similarity	NPD7327	Approved
0.7064	Intermediate Similarity	NPD7320	Approved
0.7043	Intermediate Similarity	NPD7516	Approved
0.6983	Remote Similarity	NPD8377	Approved
0.6983	Remote Similarity	NPD8294	Approved
0.6964	Remote Similarity	NPD6053	Discontinued
0.6952	Remote Similarity	NPD7638	Approved
0.6923	Remote Similarity	NPD8378	Approved
0.6923	Remote Similarity	NPD8380	Approved
0.6923	Remote Similarity	NPD8335	Approved
0.6923	Remote Similarity	NPD8379	Approved
0.6923	Remote Similarity	NPD8296	Approved
0.6887	Remote Similarity	NPD7640	Approved
0.6887	Remote Similarity	NPD7639	Approved
0.6881	Remote Similarity	NPD6402	Approved
0.6881	Remote Similarity	NPD5739	Approved
0.6881	Remote Similarity	NPD6675	Approved
0.6881	Remote Similarity	NPD7128	Approved
0.6863	Remote Similarity	NPD8035	Phase 2
0.6863	Remote Similarity	NPD8034	Phase 2
0.6838	Remote Similarity	NPD6319	Approved
0.6837	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7524	Approved
0.678	Remote Similarity	NPD7503	Approved
0.6777	Remote Similarity	NPD7078	Approved
0.6771	Remote Similarity	NPD7525	Registered
0.6768	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6881	Approved
0.6757	Remote Similarity	NPD6899	Approved
0.6754	Remote Similarity	NPD8133	Approved
0.6754	Remote Similarity	NPD4632	Approved
0.675	Remote Similarity	NPD7492	Approved
0.6735	Remote Similarity	NPD6695	Phase 3
0.6727	Remote Similarity	NPD6008	Approved
0.6698	Remote Similarity	NPD6084	Phase 2
0.6698	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD6373	Approved
0.6696	Remote Similarity	NPD6372	Approved
0.6695	Remote Similarity	NPD6059	Approved
0.6695	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6639	Remote Similarity	NPD8293	Discontinued
0.6637	Remote Similarity	NPD7102	Approved
0.6637	Remote Similarity	NPD7290	Approved
0.6637	Remote Similarity	NPD6883	Approved
0.6635	Remote Similarity	NPD6399	Phase 3
0.6634	Remote Similarity	NPD4250	Approved
0.6634	Remote Similarity	NPD4251	Approved
0.6585	Remote Similarity	NPD7736	Approved
0.6583	Remote Similarity	NPD6370	Approved
0.6579	Remote Similarity	NPD8130	Phase 1
0.6579	Remote Similarity	NPD6650	Approved
0.6579	Remote Similarity	NPD6847	Approved
0.6579	Remote Similarity	NPD6649	Approved
0.6579	Remote Similarity	NPD6869	Approved
0.6579	Remote Similarity	NPD6617	Approved
0.6549	Remote Similarity	NPD6012	Approved
0.6549	Remote Similarity	NPD6013	Approved
0.6549	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD7637	Suspended
0.6535	Remote Similarity	NPD4249	Approved
0.6532	Remote Similarity	NPD7319	Approved
0.6526	Remote Similarity	NPD6933	Approved
0.6522	Remote Similarity	NPD6882	Approved
0.6514	Remote Similarity	NPD5344	Discontinued
0.6509	Remote Similarity	NPD5695	Phase 3
0.6505	Remote Similarity	NPD6051	Approved
0.65	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD6015	Approved
0.6491	Remote Similarity	NPD6371	Approved
0.6491	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD7750	Discontinued
0.646	Remote Similarity	NPD6011	Approved
0.6455	Remote Similarity	NPD7632	Discontinued
0.6446	Remote Similarity	NPD5988	Approved
0.6441	Remote Similarity	NPD6009	Approved
0.6436	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4822	Approved
0.6429	Remote Similarity	NPD4821	Approved
0.6429	Remote Similarity	NPD4820	Approved
0.6429	Remote Similarity	NPD6928	Phase 2
0.6429	Remote Similarity	NPD6931	Approved
0.6429	Remote Similarity	NPD4819	Approved
0.6429	Remote Similarity	NPD6930	Phase 2
0.6429	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6903	Approved
0.64	Remote Similarity	NPD4788	Approved
0.6393	Remote Similarity	NPD7604	Phase 2
0.6392	Remote Similarity	NPD6115	Approved
0.6392	Remote Similarity	NPD6118	Approved
0.6392	Remote Similarity	NPD6114	Approved
0.6392	Remote Similarity	NPD6697	Approved
0.6389	Remote Similarity	NPD4755	Approved
0.6372	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5983	Phase 2
0.6364	Remote Similarity	NPD1700	Approved
0.6355	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4225	Approved
0.633	Remote Similarity	NPD5696	Approved
0.6327	Remote Similarity	NPD6929	Approved
0.6321	Remote Similarity	NPD4202	Approved
0.6321	Remote Similarity	NPD8171	Discontinued
0.6316	Remote Similarity	NPD6926	Approved
0.6316	Remote Similarity	NPD6924	Approved
0.6316	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7115	Discovery
0.63	Remote Similarity	NPD6435	Approved
0.629	Remote Similarity	NPD6336	Discontinued
0.6289	Remote Similarity	NPD6116	Phase 1
0.6289	Remote Similarity	NPD6932	Approved
0.6273	Remote Similarity	NPD5285	Approved
0.6273	Remote Similarity	NPD5286	Approved
0.6273	Remote Similarity	NPD4700	Approved
0.6273	Remote Similarity	NPD4696	Approved
0.6263	Remote Similarity	NPD4748	Discontinued
0.6261	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD6942	Approved
0.6238	Remote Similarity	NPD5362	Discontinued
0.6238	Remote Similarity	NPD5331	Approved
0.6238	Remote Similarity	NPD5332	Approved
0.6226	Remote Similarity	NPD7087	Discontinued
0.6224	Remote Similarity	NPD4268	Approved
0.6224	Remote Similarity	NPD4271	Approved
0.6218	Remote Similarity	NPD6274	Approved
0.6214	Remote Similarity	NPD7334	Approved
0.6214	Remote Similarity	NPD5330	Approved
0.6214	Remote Similarity	NPD7521	Approved
0.6214	Remote Similarity	NPD6409	Approved
0.6214	Remote Similarity	NPD6684	Approved
0.6214	Remote Similarity	NPD7146	Approved
0.62	Remote Similarity	NPD4790	Discontinued
0.6198	Remote Similarity	NPD7101	Approved
0.6198	Remote Similarity	NPD7100	Approved
0.619	Remote Similarity	NPD4753	Phase 2
0.619	Remote Similarity	NPD6033	Approved
0.6186	Remote Similarity	NPD6117	Approved
0.6176	Remote Similarity	NPD4786	Approved
0.6174	Remote Similarity	NPD6686	Approved
0.6162	Remote Similarity	NPD6683	Phase 2
0.6161	Remote Similarity	NPD5226	Approved
0.6161	Remote Similarity	NPD4633	Approved
0.6161	Remote Similarity	NPD5211	Phase 2
0.6161	Remote Similarity	NPD5225	Approved
0.6161	Remote Similarity	NPD5224	Approved
0.6146	Remote Similarity	NPD4784	Approved
0.6146	Remote Similarity	NPD4785	Approved
0.6129	Remote Similarity	NPD6067	Discontinued
0.6126	Remote Similarity	NPD6648	Approved
0.6122	Remote Similarity	NPD6925	Approved
0.6122	Remote Similarity	NPD5776	Phase 2
0.6121	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6893	Approved
0.6116	Remote Similarity	NPD6335	Approved
0.6106	Remote Similarity	NPD5175	Approved
0.6106	Remote Similarity	NPD5174	Approved
0.6105	Remote Similarity	NPD4243	Approved
0.61	Remote Similarity	NPD7514	Phase 3
0.61	Remote Similarity	NPD5368	Approved
0.61	Remote Similarity	NPD7509	Discontinued
0.6098	Remote Similarity	NPD6909	Approved
0.6098	Remote Similarity	NPD6908	Approved
0.6095	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3702	Approved
0.6075	Remote Similarity	NPD5281	Approved
0.6075	Remote Similarity	NPD5284	Approved
0.6071	Remote Similarity	NPD5223	Approved
0.6061	Remote Similarity	NPD7145	Approved
0.6058	Remote Similarity	NPD6098	Approved
0.6053	Remote Similarity	NPD5141	Approved
0.6053	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5369	Approved
0.6038	Remote Similarity	NPD6904	Approved
0.6038	Remote Similarity	NPD6673	Approved
0.6038	Remote Similarity	NPD6080	Approved
0.6038	Remote Similarity	NPD5328	Approved
0.6038	Remote Similarity	NPD1695	Approved
0.6033	Remote Similarity	NPD6317	Approved
0.6019	Remote Similarity	NPD3666	Approved
0.6019	Remote Similarity	NPD3133	Approved
0.6019	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD7645	Phase 2
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4768	Approved
0.5984	Remote Similarity	NPD6314	Approved
0.5984	Remote Similarity	NPD6313	Approved
0.5981	Remote Similarity	NPD46	Approved
0.5981	Remote Similarity	NPD7838	Discovery

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