NPASS Compound

Natural Product: NPC209430

Natural Product ID	NPC209430
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	24-Methylenecholest-4-En-3-Beta,6Beta-Diol
IUPAC Name	(3S,6R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL479912
PubChem CID	11486817
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 76 79 0 0 0 0 0 0 0 0999 V2000 5.3440 1.9087 -2.3927 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4667 0.9088 -1.4828 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1202 1.2259 -0.2134 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4031 0.4272 -0.0118 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3044 1.0600 1.0207 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9677 -0.4186 -1.9087 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8175 -0.9578 -1.1532 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5573 -0.0891 -1.2203 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4667 -0.7464 -0.4219 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8627 -0.9164 1.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5989 -0.7848 1.8492 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4527 -0.8500 0.8320 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1722 -0.0718 -0.3395 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3157 1.3831 0.0324 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7604 -0.2371 -1.4961 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0960 -0.8080 -1.2258 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6952 -0.6441 0.1096 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7251 -0.1155 1.1515 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2544 -0.3836 2.5392 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5484 0.4049 2.6798 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4513 0.0315 1.5678 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6656 -0.3662 1.8748 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7306 -0.7852 0.9349 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4172 -0.2590 -0.4222 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9820 -0.6552 -0.7382 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0147 0.0959 0.1641 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9116 1.4896 -0.3793 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9492 -0.2849 1.4303 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3089 1.7702 2.7484 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1293 -0.0299 -2.6674 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8780 1.7635 -3.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7395 2.8690 -2.1106 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4704 2.3011 -0.2145 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7325 0.6460 1.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2008 -0.6445 -0.0879 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2124 0.7862 -0.6714 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2697 1.4042 0.9052 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3017 0.0427 1.4354 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7189 1.6939 1.8697 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8751 -1.1026 -1.8019 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8019 -0.4434 -3.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5661 -1.9659 -1.6250 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0839 -1.2121 -0.1295 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8330 0.9118 -0.9091 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3536 -1.7789 -0.8310 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2921 -1.9275 1.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5371 -0.1129 1.3919 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5902 0.0961 2.5080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4883 -1.6717 2.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6180 -1.8649 0.4700 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5810 1.9149 -0.4098 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3035 1.5629 1.1204 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1789 1.8936 -0.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8932 0.7766 -1.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3229 -0.8489 -2.3411 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0843 -1.8936 -1.5601 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8184 -0.3488 -1.9687 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9539 -1.6807 0.4942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6479 0.9768 1.0303 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5004 -1.4418 2.6860 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5389 0.0243 3.2657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9655 0.1120 3.6706 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9907 -0.4193 2.9455 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7724 -1.9039 0.9577 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5722 0.8255 -0.4296 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0533 -0.7748 -1.1569 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8415 -0.3780 -1.8091 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8991 -1.7401 -0.6516 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6982 2.2526 0.3862 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0956 1.5287 -1.1201 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8412 1.7939 -0.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1609 -0.8811 2.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3513 1.9524 2.6911 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3363 0.7378 -2.8344 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8975 -1.0201 -3.1055 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9766 0.3446 -3.3217 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 3 5 1 0 2 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 1 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 23 28 1 0 20 29 1 0 8 30 1 0 13 9 1 0 26 17 1 0 18 12 1 0 26 21 1 0 1 31 1 0 1 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 4 36 1 0 5 37 1 0 5 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 7 42 1 0 7 43 1 0 8 44 1 1 9 45 1 6 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 12 50 1 6 14 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 1 18 59 1 6 19 60 1 0 19 61 1 0 20 62 1 1 22 63 1 0 23 64 1 6 24 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 27 69 1 0 27 70 1 0 27 71 1 0 28 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 M END

Standard InCHIKey	HTLJJZSYTBKDHR-JOCBKWKSSA-N
Standard InCHI	InChI=1S/C28H46O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-16-26(30)25-15-20(29)11-13-28(25,6)24(21)12-14-27(22,23)5/h15,17,19-24,26,29-30H,3,7-14,16H2,1-2,4-6H3/t19-,20+,21+,22-,23+,24+,26-,27-,28-/m1/s1
SMILES	C=C(C(C)C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@H](C2=C[C@H](CC[C@]12C)O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	414.35	Volume:	470.926 ? Van der Waals volume.
Dense:	0.88	LogP:	6.152 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.722 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.566 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	21.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.502	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.701	Fsp³:	0.857
MCE-18:	72.154 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.905	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.422	Promiscuous compounds:	0.201

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.031	MDCK Permeability:	-4.984
Pgp-inhibitor:	0.015	Pgp-substrate:	0.016
PAMPA:	0.019 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.682	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.185
Plasma Protein Binding (PPB):	95.066%	Volume Distribution (VD):	-0.195
Fu:	5.695% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.539
BSEP inhibitor:	0.59

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.642
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.144
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.993
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.984 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

11.098

Half-life (T1/2):

1.196

ADMET: Toxicity

hERG Blockers:	0.185	hERG Blockers (10um):	0.527
Human Hepatotoxicity (H-HT):	0.663	Drug-induced Liver Injury (DILI):	0.339
AMES Toxicity:	0.289	Rat Oral Acute Toxicity:	0.327
Maximum Recommended Daily Dose:	0.939	Skin Sensitization:	0.736
Carcinogencity:	0.529	Eye Corrosion:	0.009
Eye Irritation:	0.643	Respiratory Toxicity:	0.931
Drug-induced Neurotoxicity:	0.13	Ototoxicity:	0.761
Hematotoxicity:	0.323	Drug-induced Nephrotoxicity:	0.683
Genotoxicity:	0.18	RPMI-8226 Immunitoxicity:	0.113
A549 Cytotoxicity:	0.178	Hek293 Cytotoxicity:	0.292
BCF:	2.698 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.519 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.457 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.203 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691710]
NPO8169	Delphinium elatum	Species	Ranunculaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18044843]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18327911]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	Kubat, Malaysia	1991	PMID[18327911]
NPO15032	Ptilonia australasica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26904921]
NPO14031	Alcyonium patagonicum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7769395]
NPO14031	Alcyonium patagonicum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7902863]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778241]
NPO6175	Colletotrichum fragariae	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14031	Alcyonium patagonicum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8169	Delphinium elatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15032	Ptilonia australasica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14472	Sinularia ovispiculata	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12810	Adenostyles alliariae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8169	Delphinium elatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8169	Delphinium elatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8169	Delphinium elatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15196	Aframomum giganteum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14753	Croton argyroglossum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12810	Adenostyles alliariae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13917	Chondrilla juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14472	Sinularia ovispiculata	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6175	Colletotrichum fragariae	Species	Glomerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18012	Pycnanthus kombo	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10242	Cladia aggregata	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15032	Ptilonia australasica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14988	Chione glabra	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13580	Ophiobolus rubellus	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14828	Iphigenia bechuanica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1188	Pteris wallichiana	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9552	Phyllobates terribilis	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10924	Stelletta globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9418	Kreysigia multiflora	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15525	Albertisia delagoensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14031	Alcyonium patagonicum	Species	n.a.	n.a.	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	Organism Name	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell line	P388	Mus musculus	IC50	=	1.0	ug.mL-1	PMID[7769395]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC209430 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	19464
0.1-0.2	26839
0.2-0.3	3296
0.3-0.4	197
0.4-0.5	52
0.5-0.6	8
0.6-0.7	0
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	Natural Product ID
0.7692	Intermediate Similarity	NPC603222
0.7273	Intermediate Similarity	NPC474047
0.5738	Remote Similarity	NPC309603
0.5593	Remote Similarity	NPC134847
0.5517	Remote Similarity	NPC244488
0.5424	Remote Similarity	NPC247325
0.541	Remote Similarity	NPC473999
0.537	Remote Similarity	NPC111234
0.5082	Remote Similarity	NPC84694
0.5082	Remote Similarity	NPC143182

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC209430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6900
0.1-0.2	2109
0.2-0.3	132
0.3-0.4	7
0.4-0.5	2
0.5-0.6	0
0.6-0.7	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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