NPASS Compound

Structure

CID322922 OpenBabel06191716172D 35 37 0 0 1 0 0 0 0 0999 V2000 -3.0000 -6.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -4.4641 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 -1.1756 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -5.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -3.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 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 -0.5878 -0.8090 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 3.2709 -2.5000 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 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5000 -3.5981 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0000 -4.4641 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 1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 0.6180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -3.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.4641 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 0.5000 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 16 2 0 0 0 0 4 17 2 0 0 0 0 6 28 1 0 0 0 0 7 9 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 28 1 0 0 0 0 14 17 1 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 17 20 1 0 0 0 0 18 5 1 6 0 0 0 19 18 1 6 0 0 0 19 25 1 0 0 0 0 20 30 1 6 0 0 0 21 27 1 0 0 0 0 21 33 1 0 0 0 0 22 14 1 6 0 0 0 22 24 1 0 0 0 0 22 34 1 0 0 0 0 23 31 2 0 0 0 0 23 33 1 0 0 0 0 24 16 1 1 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 26 28 1 0 0 0 0 26 34 1 0 0 0 0 27 32 2 0 0 0 0 27 35 1 0 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.31
Volume:	518.16
LogP:	3.547
LogD:	3.51
LogS:	-3.213
# Rotatable Bonds:	10
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.388
Synthetic Accessibility Score:	6.262
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.781
MDCK Permeability:	0.00013368162035476416
Pgp-inhibitor:	0.005
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.081
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	75.35624694824219%
Volume Distribution (VD):	0.787
Pgp-substrate:	13.924699783325195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.68
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.479
CYP3A4-substrate:	0.435

ADMET: Excretion

Clearance (CL):	7.728
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.144
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.846
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.526
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.063
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.405

Download Data

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

Natural Product: NPC322922

Natural Product ID:	NPC322922
*Common Name:**	Hirsutalin C
IUPAC Name:	n.a.
Synonyms:	Hirsutalin C
Standard InCHIKey:	WGQGOTJWEADVEY-QXVCFRDDSA-N
Standard InCHI:	InChI=1S/C28H44O7/c1-7-9-23(31)33-21(8-2)27(32)35-28(6)13-12-20(30)17(4)14-22-24-16(3)10-11-19(18(5)15-29)25(24)26(28)34-22/h18-22,24-26,29-30H,3-4,7-15H2,1-2,5-6H3/t18-,19+,20-,21?,22+,24+,25+,26+,28+/m0/s1
SMILES:	CCCC(=O)OC(CC)C(=O)OC1(CCC(C(=C)CC2C3C(C1O2)C(CCC3=C)C(C)CO)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1631449
PubChem CID:	50900040
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002916] Eunicellane and asbestinane diterpenoids

*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
NPO16112	Cladiella hirsuta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20979397]
NPO16112	Cladiella hirsuta	Species	Alcyoniidae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	43.6	%	PMID[511225]

☑ 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 NPC322922 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	174
0.1-0.2	1433
0.2-0.3	5706
0.3-0.4	14977
0.4-0.5	8073
0.5-0.6	8725
0.6-0.7	3466
0.7-0.8	109
0.8-0.85	13
0.85-0.9	15
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC321812
0.9375	High Similarity	NPC77003
0.9146	High Similarity	NPC239308
0.9146	High Similarity	NPC5958
0.9059	High Similarity	NPC92370
0.8966	High Similarity	NPC208839
0.8953	High Similarity	NPC291875
0.8929	High Similarity	NPC471379
0.8929	High Similarity	NPC196911
0.8902	High Similarity	NPC118116
0.8851	High Similarity	NPC312471
0.8851	High Similarity	NPC471378
0.8824	High Similarity	NPC475684
0.8795	High Similarity	NPC103171
0.8721	High Similarity	NPC44538
0.8621	High Similarity	NPC470260
0.8621	High Similarity	NPC476724
0.8621	High Similarity	NPC75443
0.8621	High Similarity	NPC476723
0.8539	High Similarity	NPC122057
0.8537	High Similarity	NPC264610
0.8523	High Similarity	NPC161560
0.8519	High Similarity	NPC329626
0.8409	Intermediate Similarity	NPC309656
0.8333	Intermediate Similarity	NPC91251
0.8333	Intermediate Similarity	NPC312805
0.8293	Intermediate Similarity	NPC293223
0.8171	Intermediate Similarity	NPC36479
0.8068	Intermediate Similarity	NPC476725
0.8046	Intermediate Similarity	NPC127917
0.7895	Intermediate Similarity	NPC111348
0.7753	Intermediate Similarity	NPC151176
0.7753	Intermediate Similarity	NPC3464
0.7753	Intermediate Similarity	NPC475963
0.7742	Intermediate Similarity	NPC471747
0.7742	Intermediate Similarity	NPC8729
0.7732	Intermediate Similarity	NPC272223
0.77	Intermediate Similarity	NPC470263
0.7684	Intermediate Similarity	NPC476720
0.7684	Intermediate Similarity	NPC322188
0.7674	Intermediate Similarity	NPC252483
0.7674	Intermediate Similarity	NPC191345
0.766	Intermediate Similarity	NPC475788
0.7556	Intermediate Similarity	NPC474780
0.7553	Intermediate Similarity	NPC165180
0.75	Intermediate Similarity	NPC157476
0.75	Intermediate Similarity	NPC76054
0.7474	Intermediate Similarity	NPC147272
0.7447	Intermediate Similarity	NPC474323
0.7447	Intermediate Similarity	NPC153853
0.7447	Intermediate Similarity	NPC48732
0.7447	Intermediate Similarity	NPC206614
0.7442	Intermediate Similarity	NPC136424
0.7426	Intermediate Similarity	NPC258532
0.7419	Intermediate Similarity	NPC58219
0.7419	Intermediate Similarity	NPC177629
0.7419	Intermediate Similarity	NPC229407
0.7419	Intermediate Similarity	NPC48824
0.7419	Intermediate Similarity	NPC254572
0.7419	Intermediate Similarity	NPC250687
0.7416	Intermediate Similarity	NPC211049
0.7404	Intermediate Similarity	NPC115257
0.7404	Intermediate Similarity	NPC161816
0.7396	Intermediate Similarity	NPC190294
0.7396	Intermediate Similarity	NPC476722
0.7391	Intermediate Similarity	NPC214315
0.7391	Intermediate Similarity	NPC475019
0.7391	Intermediate Similarity	NPC474949
0.7386	Intermediate Similarity	NPC192999
0.7386	Intermediate Similarity	NPC476438
0.7368	Intermediate Similarity	NPC329952
0.7368	Intermediate Similarity	NPC198054
0.7368	Intermediate Similarity	NPC235051
0.7363	Intermediate Similarity	NPC102048
0.7347	Intermediate Similarity	NPC474313
0.7347	Intermediate Similarity	NPC323421
0.7347	Intermediate Similarity	NPC328562
0.7347	Intermediate Similarity	NPC473244
0.734	Intermediate Similarity	NPC92974
0.734	Intermediate Similarity	NPC474951
0.734	Intermediate Similarity	NPC269267
0.734	Intermediate Similarity	NPC173926
0.734	Intermediate Similarity	NPC194642
0.7333	Intermediate Similarity	NPC473921
0.7333	Intermediate Similarity	NPC475668
0.7333	Intermediate Similarity	NPC475480
0.7326	Intermediate Similarity	NPC12696
0.732	Intermediate Similarity	NPC475900
0.7312	Intermediate Similarity	NPC186148
0.7312	Intermediate Similarity	NPC179659
0.7308	Intermediate Similarity	NPC475922
0.7308	Intermediate Similarity	NPC42662
0.73	Intermediate Similarity	NPC216911
0.7292	Intermediate Similarity	NPC99653
0.7283	Intermediate Similarity	NPC329749
0.7283	Intermediate Similarity	NPC47958
0.7283	Intermediate Similarity	NPC149725
0.7283	Intermediate Similarity	NPC164424
0.7283	Intermediate Similarity	NPC304509
0.7273	Intermediate Similarity	NPC43463
0.7273	Intermediate Similarity	NPC3852
0.7264	Intermediate Similarity	NPC473877
0.7263	Intermediate Similarity	NPC474761
0.7263	Intermediate Similarity	NPC65359
0.7263	Intermediate Similarity	NPC471371
0.7263	Intermediate Similarity	NPC476004
0.7263	Intermediate Similarity	NPC471370
0.7255	Intermediate Similarity	NPC220964
0.7255	Intermediate Similarity	NPC475676
0.7253	Intermediate Similarity	NPC128246
0.7245	Intermediate Similarity	NPC476009
0.7245	Intermediate Similarity	NPC31645
0.7245	Intermediate Similarity	NPC158416
0.7245	Intermediate Similarity	NPC256227
0.7245	Intermediate Similarity	NPC284518
0.7245	Intermediate Similarity	NPC39859
0.7245	Intermediate Similarity	NPC76862
0.7245	Intermediate Similarity	NPC470883
0.7238	Intermediate Similarity	NPC5103
0.7238	Intermediate Similarity	NPC475563
0.7238	Intermediate Similarity	NPC475134
0.7234	Intermediate Similarity	NPC255176
0.7222	Intermediate Similarity	NPC126248
0.7222	Intermediate Similarity	NPC474046
0.7222	Intermediate Similarity	NPC470628
0.7222	Intermediate Similarity	NPC119922
0.7222	Intermediate Similarity	NPC259306
0.7222	Intermediate Similarity	NPC474734
0.7222	Intermediate Similarity	NPC116320
0.7216	Intermediate Similarity	NPC472360
0.7216	Intermediate Similarity	NPC476716
0.7216	Intermediate Similarity	NPC472416
0.7212	Intermediate Similarity	NPC474664
0.7212	Intermediate Similarity	NPC233379
0.7212	Intermediate Similarity	NPC14862
0.7204	Intermediate Similarity	NPC162071
0.7204	Intermediate Similarity	NPC202394
0.7204	Intermediate Similarity	NPC476015
0.7204	Intermediate Similarity	NPC474762
0.72	Intermediate Similarity	NPC476320
0.72	Intermediate Similarity	NPC476211
0.7196	Intermediate Similarity	NPC469454
0.7196	Intermediate Similarity	NPC469496
0.7196	Intermediate Similarity	NPC469463
0.7188	Intermediate Similarity	NPC184463
0.7188	Intermediate Similarity	NPC124374
0.7188	Intermediate Similarity	NPC30515
0.7188	Intermediate Similarity	NPC473675
0.7188	Intermediate Similarity	NPC41838
0.7188	Intermediate Similarity	NPC469627
0.7184	Intermediate Similarity	NPC475802
0.7184	Intermediate Similarity	NPC474101
0.7184	Intermediate Similarity	NPC127609
0.7174	Intermediate Similarity	NPC97505
0.7172	Intermediate Similarity	NPC473963
0.7159	Intermediate Similarity	NPC40049
0.7159	Intermediate Similarity	NPC469867
0.7159	Intermediate Similarity	NPC476719
0.7158	Intermediate Similarity	NPC253618
0.7158	Intermediate Similarity	NPC77001
0.7158	Intermediate Similarity	NPC246028
0.7158	Intermediate Similarity	NPC307411
0.7157	Intermediate Similarity	NPC475623
0.7157	Intermediate Similarity	NPC329834
0.7157	Intermediate Similarity	NPC474165
0.7157	Intermediate Similarity	NPC61442
0.7157	Intermediate Similarity	NPC473694
0.7157	Intermediate Similarity	NPC69171
0.7157	Intermediate Similarity	NPC474775
0.7157	Intermediate Similarity	NPC4620
0.7157	Intermediate Similarity	NPC469985
0.7157	Intermediate Similarity	NPC475334
0.7143	Intermediate Similarity	NPC259042
0.7143	Intermediate Similarity	NPC36954
0.7143	Intermediate Similarity	NPC241047
0.7143	Intermediate Similarity	NPC141350
0.7143	Intermediate Similarity	NPC15218
0.7143	Intermediate Similarity	NPC157686
0.7143	Intermediate Similarity	NPC86893
0.7143	Intermediate Similarity	NPC292178
0.713	Intermediate Similarity	NPC469877
0.713	Intermediate Similarity	NPC470919
0.7129	Intermediate Similarity	NPC27474
0.7129	Intermediate Similarity	NPC476228
0.7129	Intermediate Similarity	NPC98225
0.7129	Intermediate Similarity	NPC308824
0.7129	Intermediate Similarity	NPC97435
0.7129	Intermediate Similarity	NPC476230
0.7128	Intermediate Similarity	NPC474174
0.7128	Intermediate Similarity	NPC251808
0.7115	Intermediate Similarity	NPC475176
0.7115	Intermediate Similarity	NPC324327
0.7115	Intermediate Similarity	NPC326994
0.7115	Intermediate Similarity	NPC194620
0.7115	Intermediate Similarity	NPC72813
0.7115	Intermediate Similarity	NPC474421
0.7113	Intermediate Similarity	NPC475912
0.7113	Intermediate Similarity	NPC26046
0.7113	Intermediate Similarity	NPC474835
0.71	Intermediate Similarity	NPC222303

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 NPC322922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	2063
0.2-0.3	3977
0.3-0.4	2039
0.4-0.5	509
0.5-0.6	314
0.6-0.7	76
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
0.6796	Remote Similarity	NPD5344	Discontinued
0.6771	Remote Similarity	NPD4250	Approved
0.6771	Remote Similarity	NPD4251	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6735	Remote Similarity	NPD6698	Approved
0.6735	Remote Similarity	NPD46	Approved
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6697	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7638	Approved
0.6602	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5778	Approved
0.66	Remote Similarity	NPD5779	Approved
0.6598	Remote Similarity	NPD7524	Approved
0.6574	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6686	Approved
0.6566	Remote Similarity	NPD7838	Discovery
0.6559	Remote Similarity	NPD4820	Approved
0.6559	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4821	Approved
0.6559	Remote Similarity	NPD4822	Approved
0.6559	Remote Similarity	NPD4819	Approved
0.6538	Remote Similarity	NPD6648	Approved
0.6526	Remote Similarity	NPD6695	Phase 3
0.6505	Remote Similarity	NPD6084	Phase 2
0.6505	Remote Similarity	NPD6083	Phase 2
0.6436	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD8133	Approved
0.6408	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6402	Approved
0.6389	Remote Similarity	NPD5739	Approved
0.6389	Remote Similarity	NPD6675	Approved
0.6389	Remote Similarity	NPD7128	Approved
0.6373	Remote Similarity	NPD5282	Discontinued
0.6354	Remote Similarity	NPD6110	Phase 1
0.6354	Remote Similarity	NPD7154	Phase 3
0.6354	Remote Similarity	NPD5362	Discontinued
0.6344	Remote Similarity	NPD4268	Approved
0.6344	Remote Similarity	NPD4271	Approved
0.6339	Remote Similarity	NPD8297	Approved
0.6337	Remote Similarity	NPD8034	Phase 2
0.6337	Remote Similarity	NPD8035	Phase 2
0.6311	Remote Similarity	NPD5695	Phase 3
0.6306	Remote Similarity	NPD6371	Approved
0.6303	Remote Similarity	NPD7492	Approved
0.6283	Remote Similarity	NPD4632	Approved
0.6273	Remote Similarity	NPD7320	Approved
0.6273	Remote Similarity	NPD6899	Approved
0.6273	Remote Similarity	NPD6881	Approved
0.6263	Remote Similarity	NPD7750	Discontinued
0.6262	Remote Similarity	NPD7632	Discontinued
0.6261	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD6616	Approved
0.6239	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD6054	Approved
0.6239	Remote Similarity	NPD6059	Approved
0.6224	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7604	Phase 2
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6372	Approved
0.6216	Remote Similarity	NPD6373	Approved
0.6211	Remote Similarity	NPD6931	Approved
0.6211	Remote Similarity	NPD6930	Phase 2
0.62	Remote Similarity	NPD5737	Approved
0.62	Remote Similarity	NPD6672	Approved
0.6198	Remote Similarity	NPD7078	Approved
0.6198	Remote Similarity	NPD8293	Discontinued
0.6195	Remote Similarity	NPD6053	Discontinued
0.6186	Remote Similarity	NPD5983	Phase 2
0.6186	Remote Similarity	NPD5332	Approved
0.6186	Remote Similarity	NPD5331	Approved
0.6182	Remote Similarity	NPD5701	Approved
0.6182	Remote Similarity	NPD6412	Phase 2
0.6182	Remote Similarity	NPD5697	Approved
0.6161	Remote Similarity	NPD7290	Approved
0.6161	Remote Similarity	NPD7102	Approved
0.6161	Remote Similarity	NPD6883	Approved
0.6148	Remote Similarity	NPD7736	Approved
0.6146	Remote Similarity	NPD4790	Discontinued
0.6146	Remote Similarity	NPD5369	Approved
0.6139	Remote Similarity	NPD6101	Approved
0.6139	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6370	Approved
0.6132	Remote Similarity	NPD5696	Approved
0.6126	Remote Similarity	NPD6011	Approved
0.6121	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6336	Discontinued
0.6106	Remote Similarity	NPD6869	Approved
0.6106	Remote Similarity	NPD6617	Approved
0.6106	Remote Similarity	NPD6649	Approved
0.6106	Remote Similarity	NPD6650	Approved
0.6106	Remote Similarity	NPD6847	Approved
0.6106	Remote Similarity	NPD8130	Phase 1
0.6106	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD6929	Approved
0.6082	Remote Similarity	NPD4270	Approved
0.6082	Remote Similarity	NPD6435	Approved
0.6082	Remote Similarity	NPD4269	Approved
0.6071	Remote Similarity	NPD6013	Approved
0.6071	Remote Similarity	NPD6012	Approved
0.6071	Remote Similarity	NPD6014	Approved
0.6061	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6882	Approved
0.605	Remote Similarity	NPD6015	Approved
0.605	Remote Similarity	NPD6016	Approved
0.602	Remote Similarity	NPD3669	Approved
0.602	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7087	Discontinued
0.6019	Remote Similarity	NPD6411	Approved
0.6018	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6	Remote Similarity	NPD1145	Discontinued
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD5988	Approved
0.5983	Remote Similarity	NPD7115	Discovery
0.598	Remote Similarity	NPD6904	Approved
0.598	Remote Similarity	NPD6080	Approved
0.598	Remote Similarity	NPD1695	Approved
0.598	Remote Similarity	NPD6673	Approved
0.596	Remote Similarity	NPD4786	Approved
0.5957	Remote Similarity	NPD6933	Approved
0.595	Remote Similarity	NPD8328	Phase 3
0.5946	Remote Similarity	NPD6008	Approved
0.5943	Remote Similarity	NPD7839	Suspended
0.5932	Remote Similarity	NPD7327	Approved
0.5932	Remote Similarity	NPD7328	Approved
0.5929	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD3168	Discontinued
0.5918	Remote Similarity	NPD3667	Approved
0.5918	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD8515	Approved
0.5917	Remote Similarity	NPD8517	Approved
0.5917	Remote Similarity	NPD6921	Approved
0.5917	Remote Similarity	NPD8033	Approved
0.5917	Remote Similarity	NPD8513	Phase 3
0.5917	Remote Similarity	NPD8516	Approved
0.5914	Remote Similarity	NPD6924	Approved
0.5914	Remote Similarity	NPD6926	Approved
0.5905	Remote Similarity	NPD7748	Approved
0.59	Remote Similarity	NPD6893	Approved
0.59	Remote Similarity	NPD5363	Approved
0.5895	Remote Similarity	NPD6925	Approved
0.5895	Remote Similarity	NPD5776	Phase 2
0.5888	Remote Similarity	NPD7902	Approved
0.5887	Remote Similarity	NPD6033	Approved
0.5882	Remote Similarity	NPD7516	Approved
0.5876	Remote Similarity	NPD5368	Approved
0.5876	Remote Similarity	NPD7514	Phase 3
0.5876	Remote Similarity	NPD7332	Phase 2
0.5876	Remote Similarity	NPD4252	Approved
0.5876	Remote Similarity	NPD7525	Registered
0.5872	Remote Similarity	NPD1700	Approved
0.5865	Remote Similarity	NPD6050	Approved
0.5865	Remote Similarity	NPD5693	Phase 1
0.5865	Remote Similarity	NPD7515	Phase 2
0.5859	Remote Similarity	NPD4788	Approved
0.5854	Remote Similarity	NPD7507	Approved
0.5849	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD7334	Approved
0.5842	Remote Similarity	NPD7146	Approved
0.5842	Remote Similarity	NPD5279	Phase 3
0.5842	Remote Similarity	NPD6684	Approved
0.5842	Remote Similarity	NPD5330	Approved
0.5842	Remote Similarity	NPD7521	Approved
0.5842	Remote Similarity	NPD6409	Approved
0.5833	Remote Similarity	NPD6115	Approved
0.5833	Remote Similarity	NPD7145	Approved
0.5833	Remote Similarity	NPD8377	Approved
0.5833	Remote Similarity	NPD6697	Approved
0.5833	Remote Similarity	NPD6118	Approved
0.5833	Remote Similarity	NPD6114	Approved
0.5833	Remote Similarity	NPD8294	Approved
0.5825	Remote Similarity	NPD4753	Phase 2
0.5825	Remote Similarity	NPD6051	Approved
0.5818	Remote Similarity	NPD5211	Phase 2
0.5816	Remote Similarity	NPD6898	Phase 1
0.58	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6335	Approved
0.5785	Remote Similarity	NPD8379	Approved
0.5785	Remote Similarity	NPD8296	Approved
0.5785	Remote Similarity	NPD8380	Approved
0.5785	Remote Similarity	NPD7503	Approved
0.5785	Remote Similarity	NPD8335	Approved
0.5785	Remote Similarity	NPD8378	Approved
0.5784	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5785	Approved
0.5769	Remote Similarity	NPD5692	Phase 3
0.5763	Remote Similarity	NPD6274	Approved
0.5761	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6685	Approved
0.5752	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.575	Remote Similarity	NPD7101	Approved
0.575	Remote Similarity	NPD7100	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