NPASS Compound

Structure

NPC201046 OpenBabel07101719252D 40 41 0 0 1 0 0 0 0 0999 V2000 -4.3202 8.2314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1645 6.5974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9277 8.8211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6957 8.6715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8858 1.8474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4861 -0.1804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9277 -1.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6784 0.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3416 1.3166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8555 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8063 2.2020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6784 6.7779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9204 7.7006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8063 5.1439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4861 1.3166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 7.3459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4861 6.0294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8555 7.3459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3416 6.0294 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9277 7.8211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9350 7.7006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9508 2.2020 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8230 0.5681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9277 -0.4751 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8230 6.7779 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9204 -0.3546 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9508 5.1439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0456 3.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0456 4.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1901 3.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1901 4.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9350 -0.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4861 7.5264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1597 -1.3255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8858 5.4985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1829 3.0524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1829 4.2935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6957 -1.3255 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 -6.9116 3.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 2 0 0 0 0 3 20 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 26 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 19 1 0 0 0 0 15 22 1 0 0 0 0 15 23 1 0 0 0 0 16 21 1 0 0 0 0 16 25 1 0 0 0 0 17 25 1 0 0 0 0 17 27 1 0 0 0 0 19 2 1 6 0 0 0 20 21 1 0 0 0 0 21 4 1 1 0 0 0 22 5 1 6 0 0 0 22 30 1 0 0 0 0 23 6 1 6 0 0 0 23 39 1 0 0 0 0 24 7 1 1 0 0 0 24 26 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 6 0 0 0 26 34 1 1 0 0 0 27 31 1 0 0 0 0 27 35 2 0 0 0 0 28 11 1 6 0 0 0 28 29 1 0 0 0 0 28 40 1 0 0 0 0 29 14 1 1 0 0 0 29 40 1 0 0 0 0 30 31 1 0 0 0 0 30 36 1 1 0 0 0 31 37 1 6 0 0 0 32 38 2 0 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.38
Volume:	604.691
LogP:	3.854
LogD:	3.828
LogS:	-4.231
# Rotatable Bonds:	0
TPSA:	136.82
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.252
Synthetic Accessibility Score:	5.711
Fsp3:	0.812
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:	-4.951
MDCK Permeability:	6.752483022864908e-05
Pgp-inhibitor:	0.946
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.235
20% Bioavailability (F20%):	0.076
30% Bioavailability (F30%):	0.893

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	75.23929595947266%
Volume Distribution (VD):	1.244
Pgp-substrate:	11.321903228759766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.131
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.397
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	13.157
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.398
Drug-inuced Liver Injury (DILI):	0.774
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.706
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.639
Carcinogencity:	0.833
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC201046

Natural Product ID:	NPC201046
*Common Name:**	Amphidinolide B6
IUPAC Name:	(1S,6S,7S,10S,12R,13S,14R,17S,19S,20E,24R,26S)-6,13,14,17-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylidene-9,27-dioxabicyclo[24.1.0]heptacos-20-ene-8,15-dione
Synonyms:	Amphidinolide B6
Standard InCHIKey:	OHRZEZYMEPODIY-CJGMVNDYSA-N
Standard InCHI:	InChI=1S/C32H54O8/c1-18-12-19(2)14-29-28(40-29)11-9-8-10-26(34)24(7)32(38)39-23(6)15-22(5)30(36)31(37)27(35)17-25(33)16-21(4)20(3)13-18/h13,19,21-26,28-31,33-34,36-37H,1,8-12,14-17H2,2-7H3/b20-13+/t19-,21+,22-,23+,24+,25+,26+,28+,29+,30+,31+/m1/s1
SMILES:	C=C1C[C@@H](C)C[C@H]2[C@H](CCCC[C@@H]([C@H](C)C(=O)O[C@@H](C)C[C@@H](C)[C@@H]([C@H](C(=O)C[C@H](C[C@H](C)/C(=C/1)/C)O)O)O)O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252928
PubChem CID:	23656974
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO33366	amphidinium sp.	Species	Gymnodiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17922551]
NPO33366	amphidinium sp.	Species	Gymnodiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17927263]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1189	Cell Line	DG-75	Homo sapiens	IC50	=	0.02	ug.mL-1	PMID[478956]

☑ 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 NPC201046 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	219
0.1-0.2	1419
0.2-0.3	5323
0.3-0.4	11896
0.4-0.5	13052
0.5-0.6	7912
0.6-0.7	2617
0.7-0.8	246
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8804	High Similarity	NPC161855
0.8791	High Similarity	NPC473291
0.8667	High Similarity	NPC478036
0.8667	High Similarity	NPC478037
0.8444	Intermediate Similarity	NPC313670
0.8315	Intermediate Similarity	NPC477959
0.8242	Intermediate Similarity	NPC316228
0.8043	Intermediate Similarity	NPC65359
0.7912	Intermediate Similarity	NPC86005
0.79	Intermediate Similarity	NPC478038
0.7865	Intermediate Similarity	NPC69469
0.7826	Intermediate Similarity	NPC476706
0.7826	Intermediate Similarity	NPC476707
0.7802	Intermediate Similarity	NPC477994
0.7802	Intermediate Similarity	NPC477993
0.7766	Intermediate Similarity	NPC469627
0.7766	Intermediate Similarity	NPC472199
0.7745	Intermediate Similarity	NPC55972
0.7745	Intermediate Similarity	NPC327286
0.7745	Intermediate Similarity	NPC169888
0.7717	Intermediate Similarity	NPC471738
0.7701	Intermediate Similarity	NPC218817
0.7701	Intermediate Similarity	NPC11796
0.7677	Intermediate Similarity	NPC164598
0.7677	Intermediate Similarity	NPC474339
0.767	Intermediate Similarity	NPC15218
0.7667	Intermediate Similarity	NPC475989
0.766	Intermediate Similarity	NPC478003
0.766	Intermediate Similarity	NPC158388
0.766	Intermediate Similarity	NPC478004
0.7647	Intermediate Similarity	NPC326994
0.7647	Intermediate Similarity	NPC474421
0.7647	Intermediate Similarity	NPC324327
0.7647	Intermediate Similarity	NPC194620
0.7647	Intermediate Similarity	NPC72813
0.7609	Intermediate Similarity	NPC164393
0.7604	Intermediate Similarity	NPC5418
0.7604	Intermediate Similarity	NPC472198
0.76	Intermediate Similarity	NPC472754
0.76	Intermediate Similarity	NPC283567
0.76	Intermediate Similarity	NPC473596
0.76	Intermediate Similarity	NPC471148
0.7579	Intermediate Similarity	NPC472197
0.7579	Intermediate Similarity	NPC476705
0.7576	Intermediate Similarity	NPC475949
0.7573	Intermediate Similarity	NPC474664
0.7573	Intermediate Similarity	NPC14862
0.7573	Intermediate Similarity	NPC233379
0.7553	Intermediate Similarity	NPC118193
0.7553	Intermediate Similarity	NPC256902
0.7549	Intermediate Similarity	NPC16313
0.7549	Intermediate Similarity	NPC9303
0.7529	Intermediate Similarity	NPC326024
0.7528	Intermediate Similarity	NPC472948
0.7527	Intermediate Similarity	NPC474765
0.7527	Intermediate Similarity	NPC179659
0.7526	Intermediate Similarity	NPC300710
0.7525	Intermediate Similarity	NPC4620
0.7525	Intermediate Similarity	NPC472755
0.75	Intermediate Similarity	NPC475206
0.75	Intermediate Similarity	NPC212486
0.75	Intermediate Similarity	NPC475922
0.75	Intermediate Similarity	NPC320089
0.75	Intermediate Similarity	NPC476660
0.75	Intermediate Similarity	NPC475310
0.75	Intermediate Similarity	NPC472753
0.75	Intermediate Similarity	NPC47880
0.75	Intermediate Similarity	NPC476270
0.7476	Intermediate Similarity	NPC477513
0.7473	Intermediate Similarity	NPC11620
0.7471	Intermediate Similarity	NPC239127
0.7453	Intermediate Similarity	NPC317687
0.7451	Intermediate Similarity	NPC472756
0.7451	Intermediate Similarity	NPC474741
0.7451	Intermediate Similarity	NPC475676
0.7451	Intermediate Similarity	NPC220964
0.7451	Intermediate Similarity	NPC231271
0.7451	Intermediate Similarity	NPC470519
0.7449	Intermediate Similarity	NPC230800
0.7449	Intermediate Similarity	NPC470883
0.7449	Intermediate Similarity	NPC180722
0.7449	Intermediate Similarity	NPC165332
0.7449	Intermediate Similarity	NPC195645
0.7449	Intermediate Similarity	NPC476315
0.7449	Intermediate Similarity	NPC473859
0.7449	Intermediate Similarity	NPC76862
0.7449	Intermediate Similarity	NPC158416
0.7449	Intermediate Similarity	NPC39859
0.7449	Intermediate Similarity	NPC255410
0.7447	Intermediate Similarity	NPC281516
0.7444	Intermediate Similarity	NPC474894
0.7429	Intermediate Similarity	NPC115257
0.7429	Intermediate Similarity	NPC161816
0.7426	Intermediate Similarity	NPC39996
0.7426	Intermediate Similarity	NPC474747
0.7426	Intermediate Similarity	NPC149371
0.7419	Intermediate Similarity	NPC469483
0.7419	Intermediate Similarity	NPC122502
0.7416	Intermediate Similarity	NPC308545
0.7416	Intermediate Similarity	NPC469747
0.7416	Intermediate Similarity	NPC263574
0.7416	Intermediate Similarity	NPC82488
0.7416	Intermediate Similarity	NPC471740
0.74	Intermediate Similarity	NPC469870
0.74	Intermediate Similarity	NPC469871
0.7396	Intermediate Similarity	NPC184463
0.7391	Intermediate Similarity	NPC471343
0.7391	Intermediate Similarity	NPC474776
0.7381	Intermediate Similarity	NPC473772
0.7379	Intermediate Similarity	NPC475802
0.7374	Intermediate Similarity	NPC476613
0.7374	Intermediate Similarity	NPC120299
0.7374	Intermediate Similarity	NPC40812
0.7374	Intermediate Similarity	NPC476612
0.7368	Intermediate Similarity	NPC475971
0.7358	Intermediate Similarity	NPC317107
0.7356	Intermediate Similarity	NPC255060
0.7356	Intermediate Similarity	NPC217725
0.7353	Intermediate Similarity	NPC475945
0.7353	Intermediate Similarity	NPC469980
0.7353	Intermediate Similarity	NPC104161
0.7353	Intermediate Similarity	NPC118902
0.7353	Intermediate Similarity	NPC475871
0.7347	Intermediate Similarity	NPC14961
0.7347	Intermediate Similarity	NPC322188
0.7347	Intermediate Similarity	NPC471141
0.7347	Intermediate Similarity	NPC107476
0.7347	Intermediate Similarity	NPC36954
0.7347	Intermediate Similarity	NPC475659
0.7347	Intermediate Similarity	NPC270013
0.734	Intermediate Similarity	NPC248602
0.734	Intermediate Similarity	NPC197333
0.734	Intermediate Similarity	NPC471739
0.7333	Intermediate Similarity	NPC103634
0.7333	Intermediate Similarity	NPC38154
0.7327	Intermediate Similarity	NPC201718
0.732	Intermediate Similarity	NPC469692
0.732	Intermediate Similarity	NPC469645
0.732	Intermediate Similarity	NPC476300
0.7312	Intermediate Similarity	NPC137033
0.7308	Intermediate Similarity	NPC26617
0.7308	Intermediate Similarity	NPC266514
0.7303	Intermediate Similarity	NPC3852
0.7303	Intermediate Similarity	NPC121200
0.73	Intermediate Similarity	NPC471144
0.73	Intermediate Similarity	NPC475653
0.7294	Intermediate Similarity	NPC42526
0.7292	Intermediate Similarity	NPC473448
0.729	Intermediate Similarity	NPC473877
0.729	Intermediate Similarity	NPC66108
0.7283	Intermediate Similarity	NPC231601
0.7283	Intermediate Similarity	NPC170377
0.7273	Intermediate Similarity	NPC279621
0.7273	Intermediate Similarity	NPC469514
0.7273	Intermediate Similarity	NPC469880
0.7273	Intermediate Similarity	NPC470899
0.7273	Intermediate Similarity	NPC476009
0.7273	Intermediate Similarity	NPC475401
0.7273	Intermediate Similarity	NPC279722
0.7263	Intermediate Similarity	NPC476704
0.7263	Intermediate Similarity	NPC476708
0.7263	Intermediate Similarity	NPC202672
0.7262	Intermediate Similarity	NPC141481
0.7262	Intermediate Similarity	NPC324981
0.7262	Intermediate Similarity	NPC473559
0.7262	Intermediate Similarity	NPC209327
0.7262	Intermediate Similarity	NPC273508
0.7262	Intermediate Similarity	NPC48218
0.7255	Intermediate Similarity	NPC474709
0.7253	Intermediate Similarity	NPC286229
0.7253	Intermediate Similarity	NPC236649
0.7253	Intermediate Similarity	NPC79277
0.7253	Intermediate Similarity	NPC21693
0.7253	Intermediate Similarity	NPC184208
0.7253	Intermediate Similarity	NPC475481
0.7253	Intermediate Similarity	NPC8538
0.7245	Intermediate Similarity	NPC121825
0.7245	Intermediate Similarity	NPC474035
0.7245	Intermediate Similarity	NPC81386
0.7245	Intermediate Similarity	NPC474247
0.7241	Intermediate Similarity	NPC474321
0.7238	Intermediate Similarity	NPC308191
0.7238	Intermediate Similarity	NPC193765
0.7238	Intermediate Similarity	NPC102843
0.7238	Intermediate Similarity	NPC473807
0.7238	Intermediate Similarity	NPC322903
0.7234	Intermediate Similarity	NPC261721
0.7234	Intermediate Similarity	NPC477015
0.7234	Intermediate Similarity	NPC472009
0.7234	Intermediate Similarity	NPC469626
0.7234	Intermediate Similarity	NPC316426
0.7234	Intermediate Similarity	NPC315395
0.7234	Intermediate Similarity	NPC475753
0.7234	Intermediate Similarity	NPC475491
0.7228	Intermediate Similarity	NPC324667
0.7228	Intermediate Similarity	NPC475053
0.7228	Intermediate Similarity	NPC167974
0.7228	Intermediate Similarity	NPC288876
0.7216	Intermediate Similarity	NPC30515
0.7216	Intermediate Similarity	NPC20713

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 NPC201046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	2055
0.2-0.3	3770
0.3-0.4	2060
0.4-0.5	683
0.5-0.6	329
0.6-0.7	47
0.7-0.8	7
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8556	High Similarity	NPD7983	Approved
0.8043	Intermediate Similarity	NPD6698	Approved
0.8043	Intermediate Similarity	NPD46	Approved
0.7849	Intermediate Similarity	NPD7838	Discovery
0.7449	Intermediate Similarity	NPD7839	Suspended
0.732	Intermediate Similarity	NPD5778	Approved
0.732	Intermediate Similarity	NPD5779	Approved
0.7308	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6101	Approved
0.7174	Intermediate Similarity	NPD6435	Approved
0.7065	Intermediate Similarity	NPD5369	Approved
0.7041	Intermediate Similarity	NPD6411	Approved
0.6988	Remote Similarity	NPD3197	Phase 1
0.6957	Remote Similarity	NPD5368	Approved
0.6944	Remote Similarity	NPD6371	Approved
0.6915	Remote Similarity	NPD7154	Phase 3
0.69	Remote Similarity	NPD5282	Discontinued
0.6881	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4269	Approved
0.6809	Remote Similarity	NPD4270	Approved
0.6796	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5786	Approved
0.67	Remote Similarity	NPD7637	Suspended
0.6695	Remote Similarity	NPD8273	Phase 1
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD7829	Approved
0.6638	Remote Similarity	NPD8513	Phase 3
0.6638	Remote Similarity	NPD8516	Approved
0.6638	Remote Similarity	NPD8517	Approved
0.6638	Remote Similarity	NPD8515	Approved
0.6638	Remote Similarity	NPD8444	Approved
0.6633	Remote Similarity	NPD4250	Approved
0.6633	Remote Similarity	NPD4251	Approved
0.6606	Remote Similarity	NPD6686	Approved
0.6598	Remote Similarity	NPD5363	Approved
0.6598	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4252	Approved
0.6562	Remote Similarity	NPD5362	Discontinued
0.6559	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6319	Approved
0.6531	Remote Similarity	NPD4249	Approved
0.6522	Remote Similarity	NPD7641	Discontinued
0.6505	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5785	Approved
0.6435	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4820	Approved
0.6421	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6413	Remote Similarity	NPD8039	Approved
0.6396	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7909	Approved
0.6392	Remote Similarity	NPD6110	Phase 1
0.6383	Remote Similarity	NPD4271	Approved
0.6383	Remote Similarity	NPD4268	Approved
0.6381	Remote Similarity	NPD6083	Phase 2
0.6381	Remote Similarity	NPD6084	Phase 2
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD8074	Phase 3
0.6364	Remote Similarity	NPD6412	Phase 2
0.6356	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5344	Discontinued
0.6337	Remote Similarity	NPD1695	Approved
0.6333	Remote Similarity	NPD8341	Approved
0.6333	Remote Similarity	NPD8299	Approved
0.6333	Remote Similarity	NPD8342	Approved
0.6333	Remote Similarity	NPD8340	Approved
0.6311	Remote Similarity	NPD6399	Phase 3
0.6303	Remote Similarity	NPD8080	Discontinued
0.6289	Remote Similarity	NPD5209	Approved
0.6281	Remote Similarity	NPD8451	Approved
0.6277	Remote Similarity	NPD4756	Discovery
0.6273	Remote Similarity	NPD5739	Approved
0.6273	Remote Similarity	NPD6402	Approved
0.6273	Remote Similarity	NPD7128	Approved
0.6273	Remote Similarity	NPD6675	Approved
0.6263	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD6372	Approved
0.623	Remote Similarity	NPD8448	Approved
0.623	Remote Similarity	NPD8293	Discontinued
0.6226	Remote Similarity	NPD7902	Approved
0.6211	Remote Similarity	NPD3732	Approved
0.62	Remote Similarity	NPD5279	Phase 3
0.6198	Remote Similarity	NPD7492	Approved
0.619	Remote Similarity	NPD5695	Phase 3
0.618	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7736	Approved
0.6176	Remote Similarity	NPD5370	Suspended
0.6174	Remote Similarity	NPD4632	Approved
0.6172	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD6899	Approved
0.6161	Remote Similarity	NPD6881	Approved
0.6154	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7115	Discovery
0.6148	Remote Similarity	NPD6616	Approved
0.614	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD8130	Phase 1
0.614	Remote Similarity	NPD6649	Approved
0.6134	Remote Similarity	NPD6059	Approved
0.6134	Remote Similarity	NPD6054	Approved
0.6106	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7078	Approved
0.6094	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6882	Approved
0.608	Remote Similarity	NPD8390	Approved
0.608	Remote Similarity	NPD8392	Approved
0.608	Remote Similarity	NPD8391	Approved
0.6078	Remote Similarity	NPD6672	Approved
0.6078	Remote Similarity	NPD5737	Approved
0.6071	Remote Similarity	NPD6685	Approved
0.6071	Remote Similarity	NPD5697	Approved
0.6071	Remote Similarity	NPD5701	Approved
0.6067	Remote Similarity	NPD7331	Phase 2
0.6061	Remote Similarity	NPD5331	Approved
0.6061	Remote Similarity	NPD5332	Approved
0.6058	Remote Similarity	NPD7515	Phase 2
0.6058	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7290	Approved
0.6053	Remote Similarity	NPD6421	Discontinued
0.6053	Remote Similarity	NPD4634	Approved
0.6053	Remote Similarity	NPD6883	Approved
0.6053	Remote Similarity	NPD7102	Approved
0.6047	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6422	Discontinued
0.6033	Remote Similarity	NPD6370	Approved
0.602	Remote Similarity	NPD4790	Discontinued
0.6019	Remote Similarity	NPD7638	Approved
0.6019	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5696	Approved
0.6019	Remote Similarity	NPD4225	Approved
0.6017	Remote Similarity	NPD7500	Approved
0.6016	Remote Similarity	NPD8415	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD6109	Phase 1
0.5984	Remote Similarity	NPD7604	Phase 2
0.5982	Remote Similarity	NPD5048	Discontinued
0.598	Remote Similarity	NPD7524	Approved
0.5965	Remote Similarity	NPD6013	Approved
0.5965	Remote Similarity	NPD6014	Approved
0.5965	Remote Similarity	NPD6012	Approved
0.5963	Remote Similarity	NPD7639	Approved
0.5963	Remote Similarity	NPD7640	Approved
0.596	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6015	Approved
0.595	Remote Similarity	NPD6016	Approved
0.595	Remote Similarity	NPD6921	Approved
0.5948	Remote Similarity	NPD6053	Discontinued
0.5943	Remote Similarity	NPD7900	Approved
0.5943	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6050	Approved
0.5904	Remote Similarity	NPD3730	Approved
0.5904	Remote Similarity	NPD3195	Phase 2
0.5904	Remote Similarity	NPD3728	Approved
0.5904	Remote Similarity	NPD4266	Approved
0.5904	Remote Similarity	NPD3194	Approved
0.5904	Remote Similarity	NPD3196	Approved
0.5902	Remote Similarity	NPD5988	Approved
0.59	Remote Similarity	NPD6695	Phase 3
0.5897	Remote Similarity	NPD8133	Approved
0.5889	Remote Similarity	NPD3704	Approved
0.5882	Remote Similarity	NPD6409	Approved
0.5882	Remote Similarity	NPD7521	Approved
0.5882	Remote Similarity	NPD6009	Approved
0.5882	Remote Similarity	NPD7334	Approved
0.5882	Remote Similarity	NPD5330	Approved
0.5882	Remote Similarity	NPD7146	Approved
0.5882	Remote Similarity	NPD6684	Approved
0.5877	Remote Similarity	NPD6011	Approved
0.5873	Remote Similarity	NPD7319	Approved
0.5865	Remote Similarity	NPD4753	Phase 2
0.5862	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4786	Approved
0.5841	Remote Similarity	NPD6008	Approved
0.5833	Remote Similarity	NPD818	Approved
0.5833	Remote Similarity	NPD819	Approved
0.5825	Remote Similarity	NPD7750	Discontinued
0.582	Remote Similarity	NPD5983	Phase 2
0.5812	Remote Similarity	NPD6912	Phase 3
0.581	Remote Similarity	NPD5692	Phase 3
0.5804	Remote Similarity	NPD5765	Approved
0.58	Remote Similarity	NPD3667	Approved
0.5783	Remote Similarity	NPD3172	Approved
0.5781	Remote Similarity	NPD7260	Phase 2
0.578	Remote Similarity	NPD4755	Approved
0.5778	Remote Similarity	NPD7341	Phase 2

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