NPASS Compound

Structure

NPC266741 OpenBabel07101719522D 38 39 0 0 1 0 0 0 0 0999 V2000 -4.6851 -1.9813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3915 0.2594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2358 -4.5293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9602 1.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9602 -6.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3155 -0.7469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4711 -5.5356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8486 -4.0418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6930 -3.5543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3915 -1.2344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7249 -3.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9204 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0042 -2.5793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3155 -4.5293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7249 -2.1506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7647 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3915 -4.0418 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9602 0.1693 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9602 -5.4455 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4711 -1.2344 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0042 -3.5543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8486 -2.0918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4711 -4.0418 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6930 -2.5793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7647 -4.7887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8046 -3.1256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.2762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8486 -1.1168 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 -1.9204 -5.2762 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8046 -2.1506 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -4.7887 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.5373 -2.0918 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3915 -5.5356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7647 -3.2949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3335 -6.1924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4711 0.2594 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 15 1 0 0 0 0 7 32 1 0 0 0 0 8 9 2 0 0 0 0 8 21 1 0 0 0 0 9 24 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 13 21 2 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 16 2 1 6 0 0 0 17 3 1 1 0 0 0 17 25 1 0 0 0 0 18 4 1 6 0 0 0 18 38 1 0 0 0 0 19 5 1 6 0 0 0 19 27 1 0 0 0 0 19 30 1 0 0 0 0 20 6 1 6 0 0 0 20 28 1 0 0 0 0 20 31 1 0 0 0 0 22 24 2 0 0 0 0 22 29 1 0 0 0 0 23 14 1 1 0 0 0 23 26 1 0 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 25 30 2 3 0 0 0 25 34 1 0 0 0 0 26 31 2 3 0 0 0 26 35 1 0 0 0 0 27 32 1 0 0 0 0 27 36 2 0 0 0 0 28 37 2 0 0 0 0 28 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	641.2
Volume:	565.648
LogP:	4.26
LogD:	3.806
LogS:	-3.987
# Rotatable Bonds:	2
TPSA:	125.04
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	5.085
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
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:	-4.663
MDCK Permeability:	1.0288114026479889e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.435
Human Intestinal Absorption (HIA):	0.055
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.841

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	92.40805053710938%
Volume Distribution (VD):	0.406
Pgp-substrate:	11.72411823272705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.21
CYP2C19-substrate:	0.275
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.236
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.227
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	6.375
Half-life (T1/2):	0.244

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.951
Drug-inuced Liver Injury (DILI):	0.861
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.83
Skin Sensitization:	0.056
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC266741

Natural Product ID:	NPC266741
*Common Name:**	Geodiamolide A
IUPAC Name:	(3S,6R,9S,12S,14E,16R,18S)-6-[(4-hydroxy-3-iodophenyl)methyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triazacyclooctadec-14-ene-2,5,8,11-tetrone
Synonyms:
Standard InCHIKey:	QMYRWKWZINECMT-SVSKSJJFSA-N
Standard InCHI:	InChI=1S/C28H40IN3O6/c1-15-10-16(2)12-18(4)38-28(37)20(6)31-26(35)23(14-21-8-9-24(33)22(29)13-21)32(7)27(36)19(5)30-25(34)17(3)11-15/h8-10,13,16-20,23,33H,11-12,14H2,1-7H3,(H,30,34)(H,31,35)/b15-10+/t16-,17-,18-,19-,20-,23+/m0/s1
SMILES:	C[C@H]1C[C@@H](C)/C=C(C)/C[C@H](C)C(=N[C@H](C(=O)N([C@@H](C(=N[C@H](C(=O)O1)C)O)Cc1ccc(c(c1)I)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492178
PubChem CID:	11814284
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO32698	cymbastela sp.	Species	Axinellidae	Eukaryota	n.a.	Papua New Guinea	n.a.	PMID[10479320]
NPO32698	cymbastela sp.	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461668]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6521	Cell Line	HEY	Homo sapiens	IC50	=	43.0	ug.mL-1	PMID[533649]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16.0	ug.mL-1	PMID[533649]

☑ 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 NPC266741 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	144
0.1-0.2	862
0.2-0.3	5098
0.3-0.4	12298
0.4-0.5	13642
0.5-0.6	9069
0.6-0.7	1125
0.7-0.8	402
0.8-0.85	49
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC81026
0.9433	High Similarity	NPC39431
0.8442	Intermediate Similarity	NPC107938
0.8442	Intermediate Similarity	NPC294516
0.844	Intermediate Similarity	NPC6570
0.8392	Intermediate Similarity	NPC476989
0.8333	Intermediate Similarity	NPC46009
0.8333	Intermediate Similarity	NPC475123
0.8333	Intermediate Similarity	NPC475204
0.8333	Intermediate Similarity	NPC40234
0.8312	Intermediate Similarity	NPC472923
0.8311	Intermediate Similarity	NPC473491
0.828	Intermediate Similarity	NPC230611
0.8264	Intermediate Similarity	NPC197921
0.8231	Intermediate Similarity	NPC16188
0.8228	Intermediate Similarity	NPC273755
0.8228	Intermediate Similarity	NPC137627
0.8228	Intermediate Similarity	NPC306804
0.8228	Intermediate Similarity	NPC248670
0.8207	Intermediate Similarity	NPC91953
0.8207	Intermediate Similarity	NPC469360
0.8205	Intermediate Similarity	NPC473502
0.8201	Intermediate Similarity	NPC296712
0.82	Intermediate Similarity	NPC262166
0.8176	Intermediate Similarity	NPC155506
0.8176	Intermediate Similarity	NPC473402
0.8176	Intermediate Similarity	NPC471165
0.8176	Intermediate Similarity	NPC26108
0.8176	Intermediate Similarity	NPC158277
0.8176	Intermediate Similarity	NPC159767
0.8176	Intermediate Similarity	NPC476227
0.8176	Intermediate Similarity	NPC279871
0.8176	Intermediate Similarity	NPC473354
0.8165	Intermediate Similarity	NPC89831
0.8162	Intermediate Similarity	NPC474862
0.8156	Intermediate Similarity	NPC246079
0.8125	Intermediate Similarity	NPC50016
0.8101	Intermediate Similarity	NPC196091
0.8092	Intermediate Similarity	NPC473580
0.8092	Intermediate Similarity	NPC476268
0.8092	Intermediate Similarity	NPC244509
0.8077	Intermediate Similarity	NPC63931
0.8038	Intermediate Similarity	NPC186617
0.8025	Intermediate Similarity	NPC269750
0.8025	Intermediate Similarity	NPC194671
0.8025	Intermediate Similarity	NPC45037
0.8013	Intermediate Similarity	NPC233702
0.8	Intermediate Similarity	NPC242159
0.8	Intermediate Similarity	NPC313694
0.8	Intermediate Similarity	NPC469243
0.7987	Intermediate Similarity	NPC473693
0.7987	Intermediate Similarity	NPC471568
0.7975	Intermediate Similarity	NPC209463
0.7961	Intermediate Similarity	NPC261934
0.7961	Intermediate Similarity	NPC56685
0.7961	Intermediate Similarity	NPC202198
0.7961	Intermediate Similarity	NPC5194
0.7947	Intermediate Similarity	NPC324081
0.7935	Intermediate Similarity	NPC244336
0.7927	Intermediate Similarity	NPC476321
0.7927	Intermediate Similarity	NPC473404
0.7911	Intermediate Similarity	NPC254700
0.791	Intermediate Similarity	NPC317254
0.7902	Intermediate Similarity	NPC326966
0.7885	Intermediate Similarity	NPC475544
0.7879	Intermediate Similarity	NPC471526
0.7848	Intermediate Similarity	NPC223207
0.7831	Intermediate Similarity	NPC294951
0.781	Intermediate Similarity	NPC319950
0.7808	Intermediate Similarity	NPC127741
0.7805	Intermediate Similarity	NPC475421
0.7799	Intermediate Similarity	NPC471771
0.7799	Intermediate Similarity	NPC304074
0.7799	Intermediate Similarity	NPC290755
0.7799	Intermediate Similarity	NPC61004
0.7778	Intermediate Similarity	NPC257390
0.7762	Intermediate Similarity	NPC478147
0.7756	Intermediate Similarity	NPC323336
0.7756	Intermediate Similarity	NPC326349
0.775	Intermediate Similarity	NPC302597
0.7725	Intermediate Similarity	NPC471050
0.7725	Intermediate Similarity	NPC471048
0.7725	Intermediate Similarity	NPC471049
0.7724	Intermediate Similarity	NPC244866
0.7707	Intermediate Similarity	NPC287757
0.7707	Intermediate Similarity	NPC319320
0.7698	Intermediate Similarity	NPC56634
0.7692	Intermediate Similarity	NPC469666
0.7687	Intermediate Similarity	NPC471264
0.7687	Intermediate Similarity	NPC471265
0.7687	Intermediate Similarity	NPC68865
0.7681	Intermediate Similarity	NPC283760
0.7679	Intermediate Similarity	NPC315542
0.7665	Intermediate Similarity	NPC470903
0.7665	Intermediate Similarity	NPC470112
0.7665	Intermediate Similarity	NPC167763
0.7654	Intermediate Similarity	NPC198254
0.7654	Intermediate Similarity	NPC274198
0.7647	Intermediate Similarity	NPC102959
0.7643	Intermediate Similarity	NPC27581
0.7643	Intermediate Similarity	NPC142577
0.7639	Intermediate Similarity	NPC325651
0.7622	Intermediate Similarity	NPC476353
0.761	Intermediate Similarity	NPC241794
0.7603	Intermediate Similarity	NPC470392
0.7602	Intermediate Similarity	NPC163961
0.7602	Intermediate Similarity	NPC240130
0.7602	Intermediate Similarity	NPC61332
0.7602	Intermediate Similarity	NPC473305
0.7602	Intermediate Similarity	NPC60516
0.76	Intermediate Similarity	NPC83289
0.76	Intermediate Similarity	NPC212850
0.76	Intermediate Similarity	NPC189724
0.7593	Intermediate Similarity	NPC280022
0.7588	Intermediate Similarity	NPC94862
0.7584	Intermediate Similarity	NPC239762
0.7584	Intermediate Similarity	NPC163392
0.7574	Intermediate Similarity	NPC118202
0.7574	Intermediate Similarity	NPC299806
0.7562	Intermediate Similarity	NPC289776
0.7562	Intermediate Similarity	NPC133470
0.7562	Intermediate Similarity	NPC191863
0.7558	Intermediate Similarity	NPC473378
0.7558	Intermediate Similarity	NPC473407
0.7546	Intermediate Similarity	NPC276506
0.7537	Intermediate Similarity	NPC474149
0.7534	Intermediate Similarity	NPC45191
0.7533	Intermediate Similarity	NPC469426
0.7533	Intermediate Similarity	NPC263493
0.7533	Intermediate Similarity	NPC269398
0.7533	Intermediate Similarity	NPC469427
0.7532	Intermediate Similarity	NPC132771
0.7518	Intermediate Similarity	NPC252878
0.7516	Intermediate Similarity	NPC135121
0.7515	Intermediate Similarity	NPC136797
0.75	Intermediate Similarity	NPC477217
0.75	Intermediate Similarity	NPC201244
0.75	Intermediate Similarity	NPC313867
0.75	Intermediate Similarity	NPC328494
0.75	Intermediate Similarity	NPC316008
0.7485	Intermediate Similarity	NPC329731
0.7485	Intermediate Similarity	NPC315388
0.7485	Intermediate Similarity	NPC4910
0.7484	Intermediate Similarity	NPC7817
0.7484	Intermediate Similarity	NPC475168
0.7483	Intermediate Similarity	NPC161069
0.7483	Intermediate Similarity	NPC139326
0.7483	Intermediate Similarity	NPC274732
0.7471	Intermediate Similarity	NPC302715
0.7471	Intermediate Similarity	NPC328763
0.7471	Intermediate Similarity	NPC65714
0.747	Intermediate Similarity	NPC196243
0.7468	Intermediate Similarity	NPC9373
0.7465	Intermediate Similarity	NPC46427
0.7464	Intermediate Similarity	NPC470544
0.7463	Intermediate Similarity	NPC258056
0.7457	Intermediate Similarity	NPC477526
0.7451	Intermediate Similarity	NPC314358
0.7447	Intermediate Similarity	NPC202521
0.7434	Intermediate Similarity	NPC476978
0.7434	Intermediate Similarity	NPC314388
0.7434	Intermediate Similarity	NPC315283
0.7423	Intermediate Similarity	NPC141957
0.7423	Intermediate Similarity	NPC328649
0.7421	Intermediate Similarity	NPC56635
0.7419	Intermediate Similarity	NPC245974
0.7417	Intermediate Similarity	NPC168113
0.7413	Intermediate Similarity	NPC307020
0.741	Intermediate Similarity	NPC311737
0.741	Intermediate Similarity	NPC38458
0.741	Intermediate Similarity	NPC470545
0.7405	Intermediate Similarity	NPC256689
0.7405	Intermediate Similarity	NPC123011
0.7403	Intermediate Similarity	NPC225648
0.7403	Intermediate Similarity	NPC247298
0.7403	Intermediate Similarity	NPC329761
0.7403	Intermediate Similarity	NPC145113
0.74	Intermediate Similarity	NPC92784
0.74	Intermediate Similarity	NPC476133
0.74	Intermediate Similarity	NPC178662
0.74	Intermediate Similarity	NPC470884
0.74	Intermediate Similarity	NPC98424
0.7396	Intermediate Similarity	NPC477637
0.7389	Intermediate Similarity	NPC473341
0.7386	Intermediate Similarity	NPC473371
0.7386	Intermediate Similarity	NPC209509
0.7386	Intermediate Similarity	NPC5620
0.7379	Intermediate Similarity	NPC319766
0.7378	Intermediate Similarity	NPC129486
0.7376	Intermediate Similarity	NPC190663
0.7376	Intermediate Similarity	NPC476183
0.7376	Intermediate Similarity	NPC476990
0.7368	Intermediate Similarity	NPC251439
0.7368	Intermediate Similarity	NPC231705
0.7368	Intermediate Similarity	NPC197682
0.7368	Intermediate Similarity	NPC176226
0.7357	Intermediate Similarity	NPC470546
0.7356	Intermediate Similarity	NPC248822
0.7351	Intermediate Similarity	NPC322526
0.7351	Intermediate Similarity	NPC46098

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 NPC266741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	101
0.1-0.2	403
0.2-0.3	860
0.3-0.4	1820
0.4-0.5	3091
0.5-0.6	2108
0.6-0.7	716
0.7-0.8	51
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
0.8099	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD3136	Phase 2
0.8079	Intermediate Similarity	NPD7131	Phase 3
0.7987	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD5745	Approved
0.7799	Intermediate Similarity	NPD8303	Discontinued
0.7778	Intermediate Similarity	NPD7303	Discontinued
0.7718	Intermediate Similarity	NPD7978	Discontinued
0.7708	Intermediate Similarity	NPD5746	Approved
0.7625	Intermediate Similarity	NPD2098	Approved
0.7593	Intermediate Similarity	NPD7485	Phase 3
0.7593	Intermediate Similarity	NPD7484	Phase 3
0.7551	Intermediate Similarity	NPD6346	Approved
0.75	Intermediate Similarity	NPD2097	Approved
0.7485	Intermediate Similarity	NPD2889	Approved
0.7485	Intermediate Similarity	NPD2888	Approved
0.7485	Intermediate Similarity	NPD2017	Approved
0.7485	Intermediate Similarity	NPD2890	Approved
0.7467	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7608	Discontinued
0.7439	Intermediate Similarity	NPD4652	Approved
0.7436	Intermediate Similarity	NPD6390	Discontinued
0.7417	Intermediate Similarity	NPD7450	Phase 2
0.7413	Intermediate Similarity	NPD4659	Approved
0.7375	Intermediate Similarity	NPD7495	Discontinued
0.7361	Intermediate Similarity	NPD3125	Approved
0.7343	Intermediate Similarity	NPD2584	Suspended
0.732	Intermediate Similarity	NPD6681	Discovery
0.7292	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7523	Phase 3
0.7273	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD8019	Approved
0.7222	Intermediate Similarity	NPD2562	Approved
0.7222	Intermediate Similarity	NPD2561	Approved
0.7219	Intermediate Similarity	NPD8173	Phase 2
0.7219	Intermediate Similarity	NPD8172	Phase 2
0.7195	Intermediate Similarity	NPD8031	Discontinued
0.7192	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4103	Phase 2
0.719	Intermediate Similarity	NPD1725	Approved
0.7163	Intermediate Similarity	NPD318	Approved
0.7163	Intermediate Similarity	NPD856	Approved
0.7163	Intermediate Similarity	NPD317	Approved
0.7163	Intermediate Similarity	NPD16	Approved
0.7152	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7451	Discontinued
0.7115	Intermediate Similarity	NPD5481	Discontinued
0.7097	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD9568	Approved
0.7092	Intermediate Similarity	NPD5292	Approved
0.7092	Intermediate Similarity	NPD5291	Approved
0.7092	Intermediate Similarity	NPD3123	Discovery
0.7089	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3421	Phase 3
0.707	Intermediate Similarity	NPD8323	Discontinued
0.7067	Intermediate Similarity	NPD1330	Phase 2
0.7067	Intermediate Similarity	NPD1329	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3554	Approved
0.7059	Intermediate Similarity	NPD3555	Approved
0.7059	Intermediate Similarity	NPD3552	Approved
0.7059	Intermediate Similarity	NPD3553	Approved
0.7051	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3536	Discontinued
0.7039	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD555	Phase 2
0.7034	Intermediate Similarity	NPD5338	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5773	Approved
0.7012	Intermediate Similarity	NPD5772	Approved
0.7006	Intermediate Similarity	NPD3400	Discontinued
0.7	Intermediate Similarity	NPD2229	Approved
0.7	Intermediate Similarity	NPD4186	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2234	Approved
0.7	Intermediate Similarity	NPD2228	Approved
0.6993	Remote Similarity	NPD3054	Approved
0.6993	Remote Similarity	NPD1759	Phase 1
0.6993	Remote Similarity	NPD3052	Approved
0.6989	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7810	Phase 3
0.6978	Remote Similarity	NPD7811	Phase 3
0.6971	Remote Similarity	NPD5946	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.694	Remote Similarity	NPD855	Approved
0.694	Remote Similarity	NPD854	Approved
0.6933	Remote Similarity	NPD2891	Approved
0.6923	Remote Similarity	NPD1758	Phase 1
0.6918	Remote Similarity	NPD6666	Approved
0.6918	Remote Similarity	NPD6667	Approved
0.6914	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7972	Discontinued
0.6908	Remote Similarity	NPD6405	Approved
0.6908	Remote Similarity	NPD6407	Approved
0.6908	Remote Similarity	NPD1423	Approved
0.6908	Remote Similarity	NPD259	Phase 1
0.6905	Remote Similarity	NPD7133	Discontinued
0.6903	Remote Similarity	NPD1753	Discontinued
0.6901	Remote Similarity	NPD255	Approved
0.6901	Remote Similarity	NPD256	Approved
0.6899	Remote Similarity	NPD6676	Phase 2
0.6894	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7613	Discontinued
0.689	Remote Similarity	NPD2513	Approved
0.6879	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5303	Approved
0.6875	Remote Similarity	NPD6853	Approved
0.6875	Remote Similarity	NPD6851	Approved
0.6875	Remote Similarity	NPD5304	Approved
0.6871	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4175	Approved
0.6867	Remote Similarity	NPD4177	Approved
0.6863	Remote Similarity	NPD826	Approved
0.6863	Remote Similarity	NPD825	Approved
0.6859	Remote Similarity	NPD2239	Approved
0.6859	Remote Similarity	NPD2240	Approved
0.6855	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3692	Discontinued
0.6848	Remote Similarity	NPD3007	Approved
0.6848	Remote Similarity	NPD5355	Approved
0.6848	Remote Similarity	NPD5356	Approved
0.6848	Remote Similarity	NPD2515	Approved
0.6846	Remote Similarity	NPD1135	Approved
0.6846	Remote Similarity	NPD1129	Approved
0.6846	Remote Similarity	NPD1133	Approved
0.6846	Remote Similarity	NPD1134	Approved
0.6846	Remote Similarity	NPD1131	Approved
0.6842	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2517	Approved
0.6824	Remote Similarity	NPD3685	Discontinued
0.6821	Remote Similarity	NPD4125	Approved
0.6815	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4648	Approved
0.681	Remote Similarity	NPD4646	Approved
0.681	Remote Similarity	NPD4647	Approved
0.6807	Remote Similarity	NPD4557	Approved
0.6803	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2245	Discovery
0.6795	Remote Similarity	NPD3480	Approved
0.6792	Remote Similarity	NPD1967	Approved
0.6792	Remote Similarity	NPD1968	Approved
0.679	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5137	Approved
0.6782	Remote Similarity	NPD5485	Approved
0.6782	Remote Similarity	NPD5484	Approved
0.6782	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4738	Phase 2
0.6776	Remote Similarity	NPD2051	Approved
0.6776	Remote Similarity	NPD2046	Approved
0.6776	Remote Similarity	NPD2048	Approved
0.6776	Remote Similarity	NPD2044	Approved
0.6776	Remote Similarity	NPD21	Approved
0.6776	Remote Similarity	NPD2045	Approved
0.6776	Remote Similarity	NPD2043	Approved
0.6776	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2047	Approved
0.6774	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2568	Approved
0.6774	Remote Similarity	NPD6073	Approved
0.6774	Remote Similarity	NPD5725	Approved
0.677	Remote Similarity	NPD2016	Approved
0.677	Remote Similarity	NPD2014	Approved
0.677	Remote Similarity	NPD2013	Approved
0.6768	Remote Similarity	NPD2052	Approved
0.6766	Remote Similarity	NPD7318	Phase 3
0.6765	Remote Similarity	NPD2516	Approved
0.676	Remote Similarity	NPD4435	Approved
0.6759	Remote Similarity	NPD2217	Approved
0.6759	Remote Similarity	NPD2218	Phase 2
0.6759	Remote Similarity	NPD316	Approved
0.6755	Remote Similarity	NPD3626	Phase 3
0.6753	Remote Similarity	NPD6623	Phase 3
0.6753	Remote Similarity	NPD8416	Discontinued
0.6752	Remote Similarity	NPD1519	Approved
0.6752	Remote Similarity	NPD1538	Phase 1
0.6752	Remote Similarity	NPD1537	Approved
0.675	Remote Similarity	NPD2219	Phase 1
0.6747	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1445	Approved
0.6739	Remote Similarity	NPD1444	Approved
0.6732	Remote Similarity	NPD598	Approved
0.6732	Remote Similarity	NPD601	Approved
0.6732	Remote Similarity	NPD597	Approved
0.6732	Remote Similarity	NPD1048	Approved
0.6731	Remote Similarity	NPD6852	Discontinued
0.673	Remote Similarity	NPD2460	Phase 3
0.673	Remote Similarity	NPD2458	Approved
0.673	Remote Similarity	NPD2459	Approved
0.6728	Remote Similarity	NPD6419	Discontinued
0.6728	Remote Similarity	NPD3985	Discontinued
0.6727	Remote Similarity	NPD22	Approved
0.6727	Remote Similarity	NPD2053	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