NPASS Compound

Structure

NPC38823 OpenBabel07101719522D 39 43 0 0 1 0 0 0 0 0999 V2000 6.7350 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4158 -2.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 -2.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 -2.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0651 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8690 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0029 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0029 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1991 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2709 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1991 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3331 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4670 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4670 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 11.9311 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0651 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3331 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6010 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3331 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6010 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 15 2 0 0 0 0 6 16 2 0 0 0 0 7 8 1 0 0 0 0 7 26 1 0 0 0 0 8 28 1 0 0 0 0 9 18 1 0 0 0 0 10 29 1 0 0 0 0 11 14 2 0 0 0 0 11 37 1 0 0 0 0 12 2 1 6 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 9 1 6 0 0 0 13 14 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 17 38 1 0 0 0 0 18 28 1 0 0 0 0 18 30 2 0 0 0 0 19 20 1 0 0 0 0 19 31 1 6 0 0 0 20 21 1 0 0 0 0 20 32 1 1 0 0 0 21 24 1 0 0 0 0 21 33 1 6 0 0 0 22 28 1 0 0 0 0 22 34 2 0 0 0 0 23 37 1 0 0 0 0 23 39 1 1 0 0 0 24 38 1 0 0 0 0 24 39 1 1 0 0 0 25 26 1 0 0 0 0 25 27 2 0 0 0 0 25 35 1 0 0 0 0 26 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.18
Volume:	513.064
LogP:	0.13
LogD:	0.096
LogS:	-2.353
# Rotatable Bonds:	7
TPSA:	195.32
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.171
Synthetic Accessibility Score:	5.036
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.165
MDCK Permeability:	3.4172979212598875e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.913
20% Bioavailability (F20%):	0.045
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.318
Plasma Protein Binding (PPB):	38.34027862548828%
Volume Distribution (VD):	0.51
Pgp-substrate:	58.646156311035156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.323
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.294

ADMET: Excretion

Clearance (CL):	0.96
Half-life (T1/2):	0.461

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.241
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.368
Maximum Recommended Daily Dose:	0.838
Skin Sensitization:	0.095
Carcinogencity:	0.906
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.519

Download Data

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

Natural Product: NPC38823

Natural Product ID:	NPC38823
*Common Name:**	Paratunamide B
IUPAC Name:	(3S,4R,4aS)-4-ethenyl-7-[2-[(3S)-3-hydroxy-2-oxo-1H-indol-3-yl]ethyl]-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4,4a,5-tetrahydropyrano[3,4-c]pyridine-6,8-dione
Synonyms:
Standard InCHIKey:	MWJJDCGSBJVCSS-FHJAXKAASA-N
Standard InCHI:	InChI=1S/C26H30N2O11/c1-2-12-13-9-18(30)28(8-7-26(36)15-5-3-4-6-16(15)27-25(26)35)22(34)14(13)11-37-23(12)39-24-21(33)20(32)19(31)17(10-29)38-24/h2-6,11-13,17,19-21,23-24,29,31-33,36H,1,7-10H2,(H,27,35)/t12-,13+,17-,19-,20+,21-,23+,24+,26+/m1/s1
SMILES:	C=C[C@@H]1[C@@H]2CC(=O)N(CC[C@@]3(c4ccccc4N=C3O)O)C(=O)C2=CO[C@H]1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505137
PubChem CID:	16091681
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO18036	Cinnamodendron axillare	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067176]
NPO18036	Cinnamodendron axillare	Species	Canellaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[476390]

☑ 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 NPC38823 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	244
0.1-0.2	1100
0.2-0.3	3084
0.3-0.4	10812
0.4-0.5	18137
0.5-0.6	8353
0.6-0.7	910
0.7-0.8	47
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC207033
0.9819	High Similarity	NPC133591
0.976	High Similarity	NPC291759
0.7829	Intermediate Similarity	NPC320064
0.7717	Intermediate Similarity	NPC475962
0.7582	Intermediate Similarity	NPC276993
0.7582	Intermediate Similarity	NPC298851
0.7582	Intermediate Similarity	NPC293255
0.7582	Intermediate Similarity	NPC181138
0.7582	Intermediate Similarity	NPC210415
0.7582	Intermediate Similarity	NPC21752
0.7405	Intermediate Similarity	NPC129624
0.7374	Intermediate Similarity	NPC311357
0.7318	Intermediate Similarity	NPC211525
0.7318	Intermediate Similarity	NPC153694
0.7295	Intermediate Similarity	NPC174788
0.7268	Intermediate Similarity	NPC278887
0.72	Intermediate Similarity	NPC474077
0.7182	Intermediate Similarity	NPC63210
0.7182	Intermediate Similarity	NPC148468
0.7182	Intermediate Similarity	NPC310403
0.7182	Intermediate Similarity	NPC263709
0.7182	Intermediate Similarity	NPC243673
0.7182	Intermediate Similarity	NPC97380
0.7135	Intermediate Similarity	NPC469462
0.7128	Intermediate Similarity	NPC28510
0.712	Intermediate Similarity	NPC470069
0.712	Intermediate Similarity	NPC52059
0.7115	Intermediate Similarity	NPC476114
0.7104	Intermediate Similarity	NPC472121
0.7102	Intermediate Similarity	NPC472100
0.705	Intermediate Similarity	NPC267414
0.7017	Intermediate Similarity	NPC161827
0.7	Intermediate Similarity	NPC317672
0.6995	Remote Similarity	NPC245741
0.6995	Remote Similarity	NPC476115
0.699	Remote Similarity	NPC477548
0.699	Remote Similarity	NPC471196
0.699	Remote Similarity	NPC471195
0.6971	Remote Similarity	NPC111732
0.6967	Remote Similarity	NPC82070
0.695	Remote Similarity	NPC329024
0.6923	Remote Similarity	NPC282092
0.6919	Remote Similarity	NPC253667
0.6919	Remote Similarity	NPC35510
0.6915	Remote Similarity	NPC59033
0.6885	Remote Similarity	NPC477157
0.6885	Remote Similarity	NPC477156
0.6884	Remote Similarity	NPC203972
0.6881	Remote Similarity	NPC160127
0.6881	Remote Similarity	NPC50997
0.6866	Remote Similarity	NPC475559
0.6856	Remote Similarity	NPC322043
0.6856	Remote Similarity	NPC327373
0.6854	Remote Similarity	NPC52254
0.6832	Remote Similarity	NPC320748
0.6832	Remote Similarity	NPC324245
0.682	Remote Similarity	NPC26928
0.6814	Remote Similarity	NPC32451
0.6812	Remote Similarity	NPC474905
0.6806	Remote Similarity	NPC475271
0.6796	Remote Similarity	NPC25442
0.6796	Remote Similarity	NPC12944
0.6791	Remote Similarity	NPC99724
0.6789	Remote Similarity	NPC248903
0.6786	Remote Similarity	NPC469460
0.6776	Remote Similarity	NPC108826
0.6769	Remote Similarity	NPC325093
0.6768	Remote Similarity	NPC316405
0.6765	Remote Similarity	NPC259098
0.6765	Remote Similarity	NPC197680
0.6765	Remote Similarity	NPC79223
0.6759	Remote Similarity	NPC148124
0.6755	Remote Similarity	NPC472106
0.6734	Remote Similarity	NPC174629
0.6732	Remote Similarity	NPC328559
0.6731	Remote Similarity	NPC156044
0.6726	Remote Similarity	NPC57453
0.6724	Remote Similarity	NPC472435
0.672	Remote Similarity	NPC476194
0.672	Remote Similarity	NPC471203
0.6717	Remote Similarity	NPC325775
0.6704	Remote Similarity	NPC472103
0.6701	Remote Similarity	NPC472331
0.6701	Remote Similarity	NPC274002
0.6701	Remote Similarity	NPC126515
0.6701	Remote Similarity	NPC318020
0.67	Remote Similarity	NPC302548
0.6684	Remote Similarity	NPC470971
0.6684	Remote Similarity	NPC477159
0.6683	Remote Similarity	NPC309498
0.6683	Remote Similarity	NPC20593
0.6683	Remote Similarity	NPC182814
0.6667	Remote Similarity	NPC204970
0.6667	Remote Similarity	NPC39822
0.6667	Remote Similarity	NPC168250
0.6667	Remote Similarity	NPC307640
0.6651	Remote Similarity	NPC292517
0.6649	Remote Similarity	NPC472101
0.6649	Remote Similarity	NPC472117
0.6649	Remote Similarity	NPC85651
0.6649	Remote Similarity	NPC472120
0.6648	Remote Similarity	NPC242000
0.6648	Remote Similarity	NPC308197
0.6638	Remote Similarity	NPC472436
0.6633	Remote Similarity	NPC328798
0.6632	Remote Similarity	NPC472114
0.6632	Remote Similarity	NPC472115
0.6632	Remote Similarity	NPC473354
0.663	Remote Similarity	NPC184161
0.6618	Remote Similarity	NPC472191
0.6617	Remote Similarity	NPC127647
0.6615	Remote Similarity	NPC49353
0.6614	Remote Similarity	NPC313757
0.6613	Remote Similarity	NPC10875
0.6613	Remote Similarity	NPC10730
0.6605	Remote Similarity	NPC162812
0.6598	Remote Similarity	NPC50016
0.6596	Remote Similarity	NPC477158
0.6596	Remote Similarity	NPC474058
0.6594	Remote Similarity	NPC472434
0.6593	Remote Similarity	NPC254798
0.6583	Remote Similarity	NPC262725
0.658	Remote Similarity	NPC273755
0.657	Remote Similarity	NPC472329
0.657	Remote Similarity	NPC472330
0.6567	Remote Similarity	NPC105055
0.6567	Remote Similarity	NPC22689
0.6566	Remote Similarity	NPC471050
0.6566	Remote Similarity	NPC294951
0.6566	Remote Similarity	NPC471049
0.6566	Remote Similarity	NPC471048
0.6562	Remote Similarity	NPC469915
0.6562	Remote Similarity	NPC257354
0.6561	Remote Similarity	NPC471053
0.6561	Remote Similarity	NPC471052
0.6561	Remote Similarity	NPC471051
0.6559	Remote Similarity	NPC473297
0.6558	Remote Similarity	NPC30570
0.6555	Remote Similarity	NPC14339
0.655	Remote Similarity	NPC473815
0.6546	Remote Similarity	NPC13367
0.6545	Remote Similarity	NPC19555
0.6543	Remote Similarity	NPC291359
0.6542	Remote Similarity	NPC326027
0.6535	Remote Similarity	NPC99891
0.6533	Remote Similarity	NPC472209
0.6531	Remote Similarity	NPC45037
0.6531	Remote Similarity	NPC475094
0.653	Remote Similarity	NPC106593
0.6519	Remote Similarity	NPC49565
0.6514	Remote Similarity	NPC140311
0.6509	Remote Similarity	NPC477160
0.65	Remote Similarity	NPC473667
0.6495	Remote Similarity	NPC244856
0.6486	Remote Similarity	NPC4108
0.6477	Remote Similarity	NPC40234
0.6476	Remote Similarity	NPC268077
0.6474	Remote Similarity	NPC476231
0.6468	Remote Similarity	NPC37957
0.6465	Remote Similarity	NPC476321
0.6462	Remote Similarity	NPC476227
0.6462	Remote Similarity	NPC477462
0.6462	Remote Similarity	NPC471165
0.6462	Remote Similarity	NPC279871
0.6462	Remote Similarity	NPC473402
0.646	Remote Similarity	NPC170751
0.6458	Remote Similarity	NPC294516
0.6458	Remote Similarity	NPC107938
0.6457	Remote Similarity	NPC289415
0.6457	Remote Similarity	NPC319995
0.6457	Remote Similarity	NPC17567
0.6455	Remote Similarity	NPC471122
0.6453	Remote Similarity	NPC473800
0.6449	Remote Similarity	NPC326333
0.6447	Remote Similarity	NPC269750
0.6447	Remote Similarity	NPC194671
0.6443	Remote Similarity	NPC230611
0.6436	Remote Similarity	NPC217294
0.6436	Remote Similarity	NPC29285
0.6432	Remote Similarity	NPC471526
0.6429	Remote Similarity	NPC475448
0.6429	Remote Similarity	NPC207971
0.6429	Remote Similarity	NPC246983
0.6429	Remote Similarity	NPC159101
0.6425	Remote Similarity	NPC71124
0.6408	Remote Similarity	NPC108804
0.6408	Remote Similarity	NPC476218
0.6406	Remote Similarity	NPC471124
0.6404	Remote Similarity	NPC473305
0.6404	Remote Similarity	NPC163961
0.6398	Remote Similarity	NPC473341
0.6396	Remote Similarity	NPC477394
0.6394	Remote Similarity	NPC5374
0.6393	Remote Similarity	NPC116519
0.6393	Remote Similarity	NPC237240
0.6393	Remote Similarity	NPC31171
0.6392	Remote Similarity	NPC475123
0.6392	Remote Similarity	NPC475204
0.6389	Remote Similarity	NPC306644

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 NPC38823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	450
0.2-0.3	693
0.3-0.4	1637
0.4-0.5	3482
0.5-0.6	2574
0.6-0.7	155
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
0.6831	Remote Similarity	NPD8417	Discontinued
0.6828	Remote Similarity	NPD2995	Approved
0.6717	Remote Similarity	NPD4951	Discontinued
0.6714	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD3067	Approved
0.66	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD8326	Phase 3
0.6528	Remote Similarity	NPD3824	Phase 1
0.6528	Remote Similarity	NPD8325	Phase 3
0.6488	Remote Similarity	NPD5582	Discontinued
0.6468	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD4430	Phase 2
0.6441	Remote Similarity	NPD2791	Discontinued
0.6422	Remote Similarity	NPD7570	Approved
0.6422	Remote Similarity	NPD7569	Approved
0.6415	Remote Similarity	NPD7584	Approved
0.6409	Remote Similarity	NPD4168	Approved
0.6402	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD4897	Phase 2
0.6339	Remote Similarity	NPD2575	Approved
0.6338	Remote Similarity	NPD7583	Approved
0.6335	Remote Similarity	NPD7600	Phase 2
0.6316	Remote Similarity	NPD6874	Approved
0.6316	Remote Similarity	NPD7810	Phase 3
0.6316	Remote Similarity	NPD7811	Phase 3
0.6316	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.631	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD7585	Approved
0.6298	Remote Similarity	NPD3605	Approved
0.6298	Remote Similarity	NPD3068	Approved
0.6293	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5042	Phase 1
0.6291	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6557	Phase 2
0.6283	Remote Similarity	NPD7599	Phase 2
0.6281	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.628	Remote Similarity	NPD7256	Discontinued
0.6276	Remote Similarity	NPD2216	Approved
0.6276	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD2215	Approved
0.6275	Remote Similarity	NPD4334	Discontinued
0.6275	Remote Similarity	NPD8025	Phase 2
0.6267	Remote Similarity	NPD8059	Phase 3
0.6267	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD3069	Approved
0.6263	Remote Similarity	NPD6395	Phase 2
0.6263	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6879	Phase 2
0.625	Remote Similarity	NPD6878	Phase 2
0.6243	Remote Similarity	NPD4120	Approved
0.6243	Remote Similarity	NPD4121	Phase 3
0.6231	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7011	Discontinued
0.623	Remote Similarity	NPD2578	Phase 3
0.6222	Remote Similarity	NPD7186	Phase 3
0.622	Remote Similarity	NPD6206	Phase 1
0.6218	Remote Similarity	NPD4871	Phase 2
0.6216	Remote Similarity	NPD8323	Discontinued
0.6214	Remote Similarity	NPD5076	Approved
0.6214	Remote Similarity	NPD5077	Approved
0.6211	Remote Similarity	NPD5741	Approved
0.6211	Remote Similarity	NPD5743	Approved
0.6211	Remote Similarity	NPD5742	Approved
0.6209	Remote Similarity	NPD4501	Approved
0.6209	Remote Similarity	NPD4500	Approved
0.6205	Remote Similarity	NPD5823	Approved
0.6203	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD5121	Approved
0.6201	Remote Similarity	NPD5119	Approved
0.6201	Remote Similarity	NPD5120	Approved
0.6198	Remote Similarity	NPD4485	Approved
0.6197	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7777	Approved
0.619	Remote Similarity	NPD6261	Phase 3
0.619	Remote Similarity	NPD7778	Approved
0.619	Remote Similarity	NPD5856	Discontinued
0.619	Remote Similarity	NPD53	Approved
0.6188	Remote Similarity	NPD5507	Approved
0.6188	Remote Similarity	NPD5506	Approved
0.6184	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD7476	Discontinued
0.6175	Remote Similarity	NPD4152	Approved
0.617	Remote Similarity	NPD7613	Discontinued
0.6166	Remote Similarity	NPD2996	Approved
0.6165	Remote Similarity	NPD2843	Phase 2
0.6165	Remote Similarity	NPD2845	Phase 2
0.6162	Remote Similarity	NPD5997	Discontinued
0.6162	Remote Similarity	NPD6676	Phase 2
0.6161	Remote Similarity	NPD6248	Phase 2
0.6161	Remote Similarity	NPD6249	Phase 2
0.6154	Remote Similarity	NPD7036	Phase 3
0.6154	Remote Similarity	NPD7035	Approved
0.615	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD3437	Discontinued
0.6142	Remote Similarity	NPD7795	Phase 2
0.614	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.614	Remote Similarity	NPD2212	Approved
0.614	Remote Similarity	NPD2210	Approved
0.6135	Remote Similarity	NPD6058	Phase 2
0.6125	Remote Similarity	NPD8370	Discontinued
0.6123	Remote Similarity	NPD4086	Phase 1
0.6122	Remote Similarity	NPD2904	Discontinued
0.6117	Remote Similarity	NPD4682	Phase 2
0.6114	Remote Similarity	NPD3125	Approved
0.6111	Remote Similarity	NPD6310	Approved
0.6111	Remote Similarity	NPD6309	Approved
0.6111	Remote Similarity	NPD6311	Approved
0.6106	Remote Similarity	NPD5214	Phase 2
0.6106	Remote Similarity	NPD8146	Phase 2
0.6106	Remote Similarity	NPD4315	Phase 2
0.6106	Remote Similarity	NPD4941	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD7396	Approved
0.6087	Remote Similarity	NPD3321	Discontinued
0.6087	Remote Similarity	NPD7797	Approved
0.6087	Remote Similarity	NPD7628	Phase 3
0.6087	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7630	Phase 3
0.6087	Remote Similarity	NPD7796	Approved
0.6085	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6063	Approved
0.608	Remote Similarity	NPD2626	Approved
0.608	Remote Similarity	NPD2628	Approved
0.608	Remote Similarity	NPD2625	Approved
0.608	Remote Similarity	NPD2627	Approved
0.608	Remote Similarity	NPD2159	Approved
0.608	Remote Similarity	NPD2160	Approved
0.6077	Remote Similarity	NPD5150	Phase 2
0.6076	Remote Similarity	NPD8468	Phase 2
0.6075	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.607	Remote Similarity	NPD6642	Approved
0.607	Remote Similarity	NPD6641	Approved
0.607	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.607	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4617	Approved
0.6067	Remote Similarity	NPD4620	Approved
0.6067	Remote Similarity	NPD5201	Approved
0.6067	Remote Similarity	NPD2613	Approved
0.6067	Remote Similarity	NPD5203	Approved
0.6065	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6885	Approved
0.6062	Remote Similarity	NPD3912	Discontinued
0.6062	Remote Similarity	NPD6886	Approved
0.6061	Remote Similarity	NPD5183	Approved
0.6061	Remote Similarity	NPD5186	Approved
0.6058	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6529	Discontinued
0.6053	Remote Similarity	NPD3277	Phase 3
0.605	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD8461	Discontinued
0.6049	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5487	Phase 1
0.6047	Remote Similarity	NPD7205	Discontinued
0.6047	Remote Similarity	NPD3802	Phase 3
0.6037	Remote Similarity	NPD7263	Phase 2
0.6035	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.603	Remote Similarity	NPD2388	Discontinued
0.6029	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD5596	Phase 2
0.6027	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5578	Approved
0.6022	Remote Similarity	NPD5185	Approved
0.6022	Remote Similarity	NPD5184	Approved
0.6022	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD5182	Approved
0.602	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5444	Phase 1
0.6019	Remote Similarity	NPD3154	Approved
0.6019	Remote Similarity	NPD7891	Discontinued
0.6019	Remote Similarity	NPD3153	Approved
0.601	Remote Similarity	NPD1663	Discontinued
0.601	Remote Similarity	NPD7890	Discontinued
0.601	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.601	Remote Similarity	NPD3778	Approved
0.6009	Remote Similarity	NPD7426	Phase 1
0.6	Remote Similarity	NPD7560	Approved
0.6	Remote Similarity	NPD3821	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3822	Approved
0.6	Remote Similarity	NPD5923	Phase 1
0.6	Remote Similarity	NPD3820	Approved
0.6	Remote Similarity	NPD4513	Discontinued
0.5991	Remote Similarity	NPD7820	Phase 3
0.599	Remote Similarity	NPD3793	Phase 3
0.599	Remote Similarity	NPD1634	Approved
0.599	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.599	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.599	Remote Similarity	NPD6483	Approved
0.599	Remote Similarity	NPD6484	Approved
0.599	Remote Similarity	NPD5811	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