NPASS Compound

Structure

NPC39431 OpenBabel07101719142D 39 40 0 0 1 0 0 0 0 0999 V2000 0.6271 5.0512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9216 2.8092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8057 5.9367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4720 0.2596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0834 4.0443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8057 -1.6328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5330 1.4947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6181 0.7474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4630 1.2352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 4.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9608 1.6641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7732 2.2108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0834 0.2596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.3039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9608 2.6397 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8057 4.9611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6271 0.7474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2385 3.5565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8057 -0.6572 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7732 1.2352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6181 2.6986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2385 0.7474 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4630 2.2108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6271 3.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7665 4.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6114 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5722 2.6397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6181 3.6742 0.0000 I 0 0 0 0 0 0 0 0 0 0 0 0 -3.6114 4.3039 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7665 -0.4878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5722 1.6641 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.3079 2.6986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4720 4.0443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1002 5.7085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2385 -0.7474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5330 2.8092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5112 -1.4046 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 14 2 0 0 0 0 7 32 1 0 0 0 0 8 9 2 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 10 14 1 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 20 2 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 14 24 1 0 0 0 0 15 2 1 6 0 0 0 15 24 1 0 0 0 0 16 3 1 1 0 0 0 16 25 1 0 0 0 0 17 4 1 6 0 0 0 17 39 1 0 0 0 0 18 5 1 6 0 0 0 18 27 1 0 0 0 0 18 30 1 0 0 0 0 19 6 1 6 0 0 0 19 28 1 0 0 0 0 19 31 1 0 0 0 0 21 23 2 0 0 0 0 21 29 1 0 0 0 0 22 13 1 1 0 0 0 22 26 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 25 30 2 3 0 0 0 25 35 1 0 0 0 0 26 31 2 3 0 0 0 26 36 1 0 0 0 0 27 32 1 0 0 0 0 27 37 2 0 0 0 0 28 38 2 0 0 0 0 28 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	655.18
Volume:	571.802
LogP:	3.382
LogD:	2.284
LogS:	-3.868
# Rotatable Bonds:	2
TPSA:	142.11
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.253
Synthetic Accessibility Score:	5.223
Fsp3:	0.536
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.729
MDCK Permeability:	2.293251600349322e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	87.67713165283203%
Volume Distribution (VD):	0.272
Pgp-substrate:	13.208477020263672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.154
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.182
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	6.409
Half-life (T1/2):	0.234

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.841
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.126
Carcinogencity:	0.082
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.643

Download Data

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

Natural Product: NPC39431

Natural Product ID:	NPC39431
*Common Name:**	Geodiamolide G
IUPAC Name:	(3S,6R,9S,12S,16R,18S)-6-[(4-hydroxy-3-iodophenyl)methyl]-3,7,9,12,16,18-hexamethyl-14-methylidene-1-oxa-4,7,10-triazacyclooctadecane-2,5,8,11,15-pentone
Synonyms:	Geodiamolide G
Standard InCHIKey:	JGALXBSQYGEYPE-BFGKGAQZSA-N
Standard InCHI:	InChI=1S/C28H38IN3O7/c1-14-10-16(3)25(35)30-18(5)27(37)32(7)22(13-20-8-9-23(33)21(29)12-20)26(36)31-19(6)28(38)39-17(4)11-15(2)24(14)34/h8-9,12,15-19,22,33H,1,10-11,13H2,2-7H3,(H,30,35)(H,31,36)/t15-,16+,17+,18+,19+,22-/m1/s1
SMILES:	C[C@@H]1OC(=O)[C@H](C)N=C(O)[C@@H](Cc2ccc(c(c2)I)O)N(C)C(=O)[C@@H](N=C([C@H](CC(=C)C(=O)[C@@H](C1)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494857
PubChem CID:	10258764
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	=	8600.0	ug.mL-1	PMID[479221]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7700.0	ug.mL-1	PMID[479221]

☑ 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 NPC39431 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	158
0.1-0.2	874
0.2-0.3	4364
0.3-0.4	12127
0.4-0.5	11093
0.5-0.6	12482
0.6-0.7	1210
0.7-0.8	360
0.8-0.85	26
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9504	High Similarity	NPC81026
0.9433	High Similarity	NPC266741
0.8375	Intermediate Similarity	NPC40234
0.8365	Intermediate Similarity	NPC294516
0.8365	Intermediate Similarity	NPC107938
0.8261	Intermediate Similarity	NPC46009
0.8261	Intermediate Similarity	NPC475123
0.8261	Intermediate Similarity	NPC475204
0.8231	Intermediate Similarity	NPC6570
0.8221	Intermediate Similarity	NPC476227
0.821	Intermediate Similarity	NPC230611
0.816	Intermediate Similarity	NPC273755
0.816	Intermediate Similarity	NPC306804
0.816	Intermediate Similarity	NPC137627
0.8137	Intermediate Similarity	NPC473502
0.8133	Intermediate Similarity	NPC91953
0.8125	Intermediate Similarity	NPC296712
0.8125	Intermediate Similarity	NPC472923
0.811	Intermediate Similarity	NPC473402
0.811	Intermediate Similarity	NPC159767
0.811	Intermediate Similarity	NPC26108
0.811	Intermediate Similarity	NPC279871
0.811	Intermediate Similarity	NPC473354
0.811	Intermediate Similarity	NPC155506
0.8067	Intermediate Similarity	NPC197921
0.8061	Intermediate Similarity	NPC50016
0.8049	Intermediate Similarity	NPC248670
0.8039	Intermediate Similarity	NPC16188
0.8013	Intermediate Similarity	NPC262166
0.8	Intermediate Similarity	NPC471165
0.8	Intermediate Similarity	NPC324081
0.7988	Intermediate Similarity	NPC89831
0.7975	Intermediate Similarity	NPC186617
0.7964	Intermediate Similarity	NPC269750
0.7964	Intermediate Similarity	NPC45037
0.7964	Intermediate Similarity	NPC194671
0.7947	Intermediate Similarity	NPC476989
0.7927	Intermediate Similarity	NPC196091
0.7927	Intermediate Similarity	NPC471568
0.7927	Intermediate Similarity	NPC473693
0.7911	Intermediate Similarity	NPC476268
0.7911	Intermediate Similarity	NPC473580
0.7901	Intermediate Similarity	NPC63931
0.7898	Intermediate Similarity	NPC56685
0.7895	Intermediate Similarity	NPC469360
0.7892	Intermediate Similarity	NPC158277
0.7885	Intermediate Similarity	NPC473491
0.787	Intermediate Similarity	NPC476321
0.787	Intermediate Similarity	NPC473404
0.7853	Intermediate Similarity	NPC61004
0.7834	Intermediate Similarity	NPC233702
0.7832	Intermediate Similarity	NPC474862
0.7826	Intermediate Similarity	NPC469243
0.7824	Intermediate Similarity	NPC471526
0.7823	Intermediate Similarity	NPC478147
0.7815	Intermediate Similarity	NPC313694
0.7815	Intermediate Similarity	NPC242159
0.7805	Intermediate Similarity	NPC209463
0.7785	Intermediate Similarity	NPC5194
0.7785	Intermediate Similarity	NPC261934
0.7785	Intermediate Similarity	NPC202198
0.7778	Intermediate Similarity	NPC294951
0.7751	Intermediate Similarity	NPC475421
0.7718	Intermediate Similarity	NPC326966
0.7718	Intermediate Similarity	NPC246079
0.7716	Intermediate Similarity	NPC475544
0.7692	Intermediate Similarity	NPC135121
0.7688	Intermediate Similarity	NPC244509
0.7683	Intermediate Similarity	NPC223207
0.7674	Intermediate Similarity	NPC471049
0.7674	Intermediate Similarity	NPC471048
0.7674	Intermediate Similarity	NPC471050
0.7657	Intermediate Similarity	NPC240130
0.7657	Intermediate Similarity	NPC61332
0.7654	Intermediate Similarity	NPC287757
0.7654	Intermediate Similarity	NPC319320
0.7636	Intermediate Similarity	NPC290755
0.7636	Intermediate Similarity	NPC254700
0.7636	Intermediate Similarity	NPC471771
0.7636	Intermediate Similarity	NPC304074
0.7632	Intermediate Similarity	NPC127741
0.7622	Intermediate Similarity	NPC319950
0.7616	Intermediate Similarity	NPC167763
0.7616	Intermediate Similarity	NPC470112
0.7616	Intermediate Similarity	NPC470903
0.76	Intermediate Similarity	NPC257390
0.76	Intermediate Similarity	NPC102959
0.759	Intermediate Similarity	NPC302597
0.7568	Intermediate Similarity	NPC476353
0.7564	Intermediate Similarity	NPC201244
0.7564	Intermediate Similarity	NPC477217
0.756	Intermediate Similarity	NPC328494
0.7557	Intermediate Similarity	NPC473305
0.7557	Intermediate Similarity	NPC163961
0.7557	Intermediate Similarity	NPC60516
0.755	Intermediate Similarity	NPC244866
0.7546	Intermediate Similarity	NPC244336
0.7532	Intermediate Similarity	NPC322526
0.7532	Intermediate Similarity	NPC239762
0.7532	Intermediate Similarity	NPC163392
0.7529	Intermediate Similarity	NPC299806
0.7529	Intermediate Similarity	NPC315542
0.7528	Intermediate Similarity	NPC65714
0.7517	Intermediate Similarity	NPC469666
0.7517	Intermediate Similarity	NPC56634
0.7516	Intermediate Similarity	NPC471265
0.7516	Intermediate Similarity	NPC471264
0.7516	Intermediate Similarity	NPC68865
0.7514	Intermediate Similarity	NPC473407
0.7514	Intermediate Similarity	NPC473378
0.75	Intermediate Similarity	NPC198254
0.75	Intermediate Similarity	NPC274198
0.7484	Intermediate Similarity	NPC269398
0.7484	Intermediate Similarity	NPC263493
0.7469	Intermediate Similarity	NPC123011
0.7469	Intermediate Similarity	NPC256689
0.7468	Intermediate Similarity	NPC473052
0.7468	Intermediate Similarity	NPC473055
0.7467	Intermediate Similarity	NPC325651
0.7466	Intermediate Similarity	NPC142577
0.7466	Intermediate Similarity	NPC27581
0.7465	Intermediate Similarity	NPC317254
0.7455	Intermediate Similarity	NPC241794
0.7444	Intermediate Similarity	NPC473371
0.7443	Intermediate Similarity	NPC4910
0.7443	Intermediate Similarity	NPC329731
0.7443	Intermediate Similarity	NPC94862
0.744	Intermediate Similarity	NPC280022
0.7436	Intermediate Similarity	NPC139326
0.7436	Intermediate Similarity	NPC161069
0.7434	Intermediate Similarity	NPC328070
0.7434	Intermediate Similarity	NPC470392
0.743	Intermediate Similarity	NPC302715
0.7419	Intermediate Similarity	NPC471201
0.7416	Intermediate Similarity	NPC477526
0.741	Intermediate Similarity	NPC191863
0.741	Intermediate Similarity	NPC289776
0.741	Intermediate Similarity	NPC133470
0.7403	Intermediate Similarity	NPC471592
0.7396	Intermediate Similarity	NPC276506
0.7389	Intermediate Similarity	NPC476978
0.7378	Intermediate Similarity	NPC323336
0.7378	Intermediate Similarity	NPC326349
0.7375	Intermediate Similarity	NPC132771
0.7372	Intermediate Similarity	NPC168113
0.7368	Intermediate Similarity	NPC45191
0.7368	Intermediate Similarity	NPC136797
0.7358	Intermediate Similarity	NPC225648
0.7358	Intermediate Similarity	NPC329761
0.7356	Intermediate Similarity	NPC477637
0.7346	Intermediate Similarity	NPC473341
0.7342	Intermediate Similarity	NPC5620
0.7342	Intermediate Similarity	NPC313867
0.7342	Intermediate Similarity	NPC316008
0.7337	Intermediate Similarity	NPC129486
0.7333	Intermediate Similarity	NPC328763
0.7329	Intermediate Similarity	NPC190663
0.7326	Intermediate Similarity	NPC196243
0.7325	Intermediate Similarity	NPC251439
0.7325	Intermediate Similarity	NPC176226
0.7325	Intermediate Similarity	NPC197682
0.7318	Intermediate Similarity	NPC248822
0.7312	Intermediate Similarity	NPC9373
0.7296	Intermediate Similarity	NPC314358
0.7293	Intermediate Similarity	NPC59827
0.7293	Intermediate Similarity	NPC184933
0.729	Intermediate Similarity	NPC109580
0.7283	Intermediate Similarity	NPC477551
0.7278	Intermediate Similarity	NPC315283
0.7278	Intermediate Similarity	NPC141957
0.7278	Intermediate Similarity	NPC314388
0.7278	Intermediate Similarity	NPC328649
0.7273	Intermediate Similarity	NPC56635
0.7268	Intermediate Similarity	NPC477552
0.7268	Intermediate Similarity	NPC477550
0.7261	Intermediate Similarity	NPC469427
0.7261	Intermediate Similarity	NPC150712
0.7261	Intermediate Similarity	NPC469426
0.726	Intermediate Similarity	NPC283760
0.725	Intermediate Similarity	NPC138775
0.725	Intermediate Similarity	NPC145113
0.7244	Intermediate Similarity	NPC476133
0.7244	Intermediate Similarity	NPC178662
0.7244	Intermediate Similarity	NPC98424
0.7244	Intermediate Similarity	NPC470884
0.7244	Intermediate Similarity	NPC92784
0.7241	Intermediate Similarity	NPC470545
0.7238	Intermediate Similarity	NPC314083
0.7235	Intermediate Similarity	NPC66490
0.7235	Intermediate Similarity	NPC315388
0.7234	Intermediate Similarity	NPC474149
0.7233	Intermediate Similarity	NPC209509
0.723	Intermediate Similarity	NPC160493
0.7222	Intermediate Similarity	NPC475168
0.7222	Intermediate Similarity	NPC7817
0.7215	Intermediate Similarity	NPC212850
0.7215	Intermediate Similarity	NPC189724
0.7215	Intermediate Similarity	NPC83289
0.7209	Intermediate Similarity	NPC475532
0.7197	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 NPC39431 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	109
0.1-0.2	406
0.2-0.3	854
0.3-0.4	1847
0.4-0.5	2981
0.5-0.6	2272
0.6-0.7	645
0.7-0.8	36
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
0.7905	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7131	Phase 3
0.7891	Intermediate Similarity	NPD3136	Phase 2
0.7812	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD8303	Discontinued
0.7533	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7484	Phase 3
0.744	Intermediate Similarity	NPD7485	Phase 3
0.7436	Intermediate Similarity	NPD7978	Discontinued
0.7434	Intermediate Similarity	NPD5745	Approved
0.7391	Intermediate Similarity	NPD7303	Discontinued
0.7365	Intermediate Similarity	NPD2098	Approved
0.7315	Intermediate Similarity	NPD3125	Approved
0.7303	Intermediate Similarity	NPD5746	Approved
0.7294	Intermediate Similarity	NPD7608	Discontinued
0.7284	Intermediate Similarity	NPD6390	Discontinued
0.7278	Intermediate Similarity	NPD6681	Discovery
0.7273	Intermediate Similarity	NPD6346	Approved
0.7261	Intermediate Similarity	NPD7450	Phase 2
0.7246	Intermediate Similarity	NPD2097	Approved
0.7239	Intermediate Similarity	NPD7523	Phase 3
0.7235	Intermediate Similarity	NPD2017	Approved
0.7235	Intermediate Similarity	NPD2889	Approved
0.7235	Intermediate Similarity	NPD2888	Approved
0.7235	Intermediate Similarity	NPD2890	Approved
0.7229	Intermediate Similarity	NPD7495	Discontinued
0.7197	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4652	Approved
0.7181	Intermediate Similarity	NPD2584	Suspended
0.7179	Intermediate Similarity	NPD8172	Phase 2
0.7179	Intermediate Similarity	NPD8173	Phase 2
0.7135	Intermediate Similarity	NPD7811	Phase 3
0.7135	Intermediate Similarity	NPD7810	Phase 3
0.7133	Intermediate Similarity	NPD4659	Approved
0.7126	Intermediate Similarity	NPD8019	Approved
0.7125	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7972	Discontinued
0.7063	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3123	Discovery
0.7039	Intermediate Similarity	NPD5946	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8323	Discontinued
0.7012	Intermediate Similarity	NPD5348	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5481	Discontinued
0.6975	Remote Similarity	NPD3400	Discontinued
0.6951	Remote Similarity	NPD6682	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9568	Approved
0.6937	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4103	Phase 2
0.6923	Remote Similarity	NPD1330	Phase 2
0.6923	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD555	Phase 2
0.6886	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD256	Approved
0.6871	Remote Similarity	NPD255	Approved
0.6868	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8031	Discontinued
0.6846	Remote Similarity	NPD1759	Phase 1
0.6842	Remote Similarity	NPD7318	Phase 3
0.6842	Remote Similarity	NPD2562	Approved
0.6842	Remote Similarity	NPD2561	Approved
0.6835	Remote Similarity	NPD825	Approved
0.6835	Remote Similarity	NPD826	Approved
0.6833	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1725	Approved
0.6829	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1670	Discontinued
0.6818	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3553	Approved
0.6813	Remote Similarity	NPD3554	Approved
0.6813	Remote Similarity	NPD3555	Approved
0.6813	Remote Similarity	NPD3552	Approved
0.6779	Remote Similarity	NPD318	Approved
0.6779	Remote Similarity	NPD1758	Phase 1
0.6779	Remote Similarity	NPD317	Approved
0.6779	Remote Similarity	NPD856	Approved
0.6779	Remote Similarity	NPD16	Approved
0.6778	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7451	Discontinued
0.6772	Remote Similarity	NPD7565	Approved
0.6772	Remote Similarity	NPD259	Phase 1
0.6768	Remote Similarity	NPD1968	Approved
0.6768	Remote Similarity	NPD1967	Approved
0.6766	Remote Similarity	NPD7613	Discontinued
0.6766	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5485	Approved
0.676	Remote Similarity	NPD5484	Approved
0.6758	Remote Similarity	NPD6853	Approved
0.6758	Remote Similarity	NPD6851	Approved
0.6755	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6039	Approved
0.6748	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3455	Phase 2
0.6735	Remote Similarity	NPD2234	Approved
0.6735	Remote Similarity	NPD2228	Approved
0.6735	Remote Similarity	NPD2229	Approved
0.6732	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4177	Approved
0.6731	Remote Similarity	NPD4175	Approved
0.673	Remote Similarity	NPD8416	Discontinued
0.6728	Remote Similarity	NPD2239	Approved
0.6728	Remote Similarity	NPD2240	Approved
0.6725	Remote Similarity	NPD5356	Approved
0.6725	Remote Similarity	NPD5355	Approved
0.6725	Remote Similarity	NPD7317	Phase 3
0.6724	Remote Similarity	NPD6862	Phase 2
0.6711	Remote Similarity	NPD3421	Phase 3
0.6711	Remote Similarity	NPD5291	Approved
0.6711	Remote Similarity	NPD5292	Approved
0.6707	Remote Similarity	NPD3536	Discontinued
0.6706	Remote Similarity	NPD2891	Approved
0.6688	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4207	Discontinued
0.6688	Remote Similarity	NPD4125	Approved
0.6687	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6666	Approved
0.6687	Remote Similarity	NPD8076	Discontinued
0.6687	Remote Similarity	NPD6667	Approved
0.6686	Remote Similarity	NPD5772	Approved
0.6686	Remote Similarity	NPD7133	Discontinued
0.6686	Remote Similarity	NPD5773	Approved
0.6667	Remote Similarity	NPD5137	Approved
0.6667	Remote Similarity	NPD2513	Approved
0.6667	Remote Similarity	NPD7695	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4807	Approved
0.6667	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4731	Phase 3
0.6667	Remote Similarity	NPD6405	Approved
0.6667	Remote Similarity	NPD6407	Approved
0.6667	Remote Similarity	NPD6676	Phase 2
0.6667	Remote Similarity	NPD4806	Approved
0.6649	Remote Similarity	NPD4435	Approved
0.6647	Remote Similarity	NPD5967	Approved
0.6646	Remote Similarity	NPD3052	Approved
0.6646	Remote Similarity	NPD6119	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6073	Approved
0.6646	Remote Similarity	NPD5725	Approved
0.6646	Remote Similarity	NPD4738	Phase 2
0.6646	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3054	Approved
0.6645	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7011	Discontinued
0.6628	Remote Similarity	NPD2515	Approved
0.6628	Remote Similarity	NPD3007	Approved
0.6626	Remote Similarity	NPD1538	Phase 1
0.6626	Remote Similarity	NPD6032	Approved
0.6626	Remote Similarity	NPD1537	Approved
0.6626	Remote Similarity	NPD1519	Approved
0.6625	Remote Similarity	NPD6623	Phase 3
0.6625	Remote Similarity	NPD8265	Approved
0.6624	Remote Similarity	NPD4208	Discontinued
0.6624	Remote Similarity	NPD3664	Approved
0.6624	Remote Similarity	NPD3663	Approved
0.6624	Remote Similarity	NPD3626	Phase 3
0.6624	Remote Similarity	NPD3662	Phase 3
0.6624	Remote Similarity	NPD3661	Approved
0.6623	Remote Similarity	NPD2218	Phase 2
0.6623	Remote Similarity	NPD5304	Approved
0.6623	Remote Similarity	NPD2217	Approved
0.6623	Remote Similarity	NPD5303	Approved
0.6611	Remote Similarity	NPD3965	Phase 1
0.661	Remote Similarity	NPD2517	Approved
0.6605	Remote Similarity	NPD5688	Approved
0.6605	Remote Similarity	NPD6852	Discontinued
0.6605	Remote Similarity	NPD6901	Phase 3
0.6605	Remote Similarity	NPD5689	Approved
0.6604	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4619	Approved
0.6604	Remote Similarity	NPD4621	Approved
0.6603	Remote Similarity	NPD1133	Approved
0.6603	Remote Similarity	NPD1131	Approved
0.6603	Remote Similarity	NPD1135	Approved
0.6603	Remote Similarity	NPD1134	Approved
0.6603	Remote Similarity	NPD1129	Approved
0.6595	Remote Similarity	NPD4434	Approved
0.659	Remote Similarity	NPD4557	Approved
0.6588	Remote Similarity	NPD8315	Phase 1
0.6588	Remote Similarity	NPD4646	Approved
0.6588	Remote Similarity	NPD4647	Approved
0.6588	Remote Similarity	NPD4648	Approved
0.6587	Remote Similarity	NPD5308	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4152	Approved
0.6585	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD8643	Discontinued
0.6582	Remote Similarity	NPD5203	Approved
0.6582	Remote Similarity	NPD4620	Approved
0.6582	Remote Similarity	NPD4617	Approved
0.6582	Remote Similarity	NPD5201	Approved
0.6581	Remote Similarity	NPD3685	Discontinued
0.6581	Remote Similarity	NPD1755	Approved
0.6578	Remote Similarity	NPD6504	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